Sean Xiao-An Zhang

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Name: 张晓安; Zhang, XiaoAn

Organization: Jilin University , China

Department: State Key Laboratory of Supramolecular Structure and Materials

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Endowing Hydrochromism to Fluorans via Bioinspired Alteration of Molecular Structures and Microenvironments and Expanding Their Potential for Rewritable Paper

Co-reporter:Guan Xi, Lan Sheng, Ivan Zhang, Jiahui Du, Ting Zhang, Qiaonan Chen, Guiying Li, Ying Zhang, Yue Song, Jianhua Li, Yu-Mo Zhang, and Sean Xiao-An Zhang

ACS Applied Materials & Interfaces November 1, 2017 Volume 9(Issue 43) pp:38032-38032

Publication Date(Web):October 12, 2017

DOI:10.1021/acsami.7b12363

Interest and effort toward new materials for rewritable paper have increased dramatically because of the exciting advantages for sustainable development and better nature life cycle. Inspired by how nature works within living systems, herein, we have used fluorans, as a concept verification, to endow original acidochromic, basochromic or photochromic molecules with broader properties, such as switchable with solvent, water, heat, electricity, stress, other force, etc., via simplified methods (i.e., via variation of submolecular structure or microenvironments). The hydrochromic visual change and reversible behavior of selected molecules have been explored, and the primary mechanism at the atomic or subatomic level has been hypothesized. In addition, several newly demonstrated hydrochromic fluorans have been utilized for water-jet rewritable paper (WJRP), which exhibit great photostability, high hydrochromic contrast, and fast responsive rate and which can be reused at least 30 times without significant variation. The water-jet prints have good resolution and various colors and can keep legibility after a few months or years. This improved performance is a major step toward practical applications of WJRP.Keywords: dynamic equilibrium; fluoran dye; hydrochromism; microenvironment; rewritable paper; water-jet prints;

Reversible Bond/Cation-Coupled Electron Transfer on Phenylenediamine-Based Rhodamine B and Its Application on Electrochromism

Co-reporter:Xiaojun Wang, Shuo Wang, Chang Gu, Weiran Zhang, Hongzhi Zheng, Jingjing Zhang, Geyu Lu, Yu-Mo Zhang, Minjie Li, and Sean Xiao-An Zhang

ACS Applied Materials & Interfaces June 14, 2017 Volume 9(Issue 23) pp:20196-20196

Publication Date(Web):May 23, 2017

DOI:10.1021/acsami.7b03199

A biomimetic system on reversible bond-coupled electron transfer (BCET) has been proposed and investigated in a switchable Rh–N molecule with redox active subunits. We discover that energy barrier of C–N bond breaking is reduced dramatically to less than 1/7 (from 40.4 to 5.5 kcal/mol), and 1/3 of the oxidation potential is simultaneously lowered (from 0.67 to 0.43 V) with the oxidation of Rh–N. The concept, cation-coupled electron transfer (CCET), is highly recommended by analyzing existing proton coupled electron transfer (PCET) and metal coupled electron transfer (MCET) along with aforementioned BCET, which have same characteristic of transferring positive charges, such as proton, metal ion, and organic cation. Molecular switch can be controlled directly by electricity through BCET process. Solid electrochromic device was fabricated with extremely high coloration efficiency (720 cm2/C), great reversibility (no degradation for 600 cycles), and quick respond time (30 ms).Keywords: bond-coupled electron transfer; cation-coupled electron transfer; electrochromic material; electron transfer; molecular switch;

Luciferin inspired oxygen sensing with alternant change of color and fluorescence

Co-reporter:Yu-Mo Zhang, Jingjing Zhang, Sean Xiao-An Zhang

Dyes and Pigments 2017 Volume 138(Volume 138) pp:

Publication Date(Web):1 March 2017

DOI:10.1016/j.dyepig.2016.11.016

•Inspired by bioluminescence of luciferin, the dual mode oxygen sensor is developed.•The mechanism containing four-member ring intermediate has been proved by MS and DFT.•The sensor strip exhibits high selective and perfect optical properties.Inspired by enol-degradation of luciferin, a new dual mode oxygen sensing with alternant change of color and fluorescence has been developed to estimate rapidly the oxygen concentration. Based on the screening of ten methyl ketone molecules with different functional groups, molecule M5 with obvious fluorescence change and high degradation speed is selected and studied in detail by UV-Vis and fluorescence spectroscopy. The degradative mechanism containing four-member ring intermediate has been proved by MS and DFT calculation. And the sensor strip prepared by molecule M5 exhibits high selective and perfect optical properties to detect the oxygen concentration without delicate instrument. This oxygen sensor will not only accelerate the development of oxygen sensor, but will also help to understand the mechanism of luciferin bio-degradation.Download high-res image (211KB)Download full-size image

Tunable RGB luminescence of a single molecule with high quantum yields through a rational design

Co-reporter:Wen Li, Yu-Mo Zhang, Ting Zhang, Weiran Zhang, Minjie Li and Sean Xiao-An Zhang

Journal of Materials Chemistry A 2016 vol. 4(Issue 7) pp:1527-1532

Publication Date(Web):12 Jan 2016

DOI:10.1039/C5TC03378K

Organic smart materials with red, green, and blue emissions are important in fabricating full-color display devices and multi-functional sensors. However, achieving RGB emission with high quantum yields using a single-molecule material has proven to be challenging. In this study, a new stimuli-responsive RGB luminescent organic molecule RHBT-G with a high quantum yield was rationally designed based on the combination of an AIEE luminophore and a fluorescent molecular switch. The ESIPT and TBET mechanisms were introduced to realize the RGB emission with single 365 nm excitation light in a solution and a PMMA film. X-ray single crystal diffraction and UV-Vis and photoluminescence (PL) spectroscopic analysis were carried out to prove the working mechanism of the dye. The rational design will accelerate the development of stimuli-responsive materials with excellent optical properties.

A methyl ketone bridged molecule as a multi-stimuli-responsive color switch for electrochromic devices

Co-reporter:Yu-Mo Zhang, Fuli Xie, Wen Li, Yuyang Wang, Weiran Zhang, Xiaojun Wang, Minjie Li and Sean Xiao-An Zhang

Journal of Materials Chemistry A 2016 vol. 4(Issue 21) pp:4662-4667

Publication Date(Web):13 Apr 2016

DOI:10.1039/C5TC04236D

A new multi-stimuli-responsive molecular switch M5 with a methyl ketone bridge has been developed to fabricate a visible-near infrared absorbing electrochromic device. The basochromic and electrochromic properties of methyl ketone M5 with nitronaphthalene were studied in detail using a spectroelectrochemical method and density functional theory (DFT) calculations. The colorless M5 can be switched to green-yellow with broad visible-near infrared absorption (400–500 nm, 550–800 nm), stimulated by base and electricity. And a multi electron transfer–proton transfer mechanism (electrobase) of electrochromism for M5 has been proved using cyclic voltammetry (CV) and in situ UV-vis spectroscopy. This multi-stimuli-responsive color switch has been successfully applied in an electrochromic device with attractive properties such as short switching time and good reversibility.

Design, synthesis and properties of near-infrared molecular switches containing a fluorene ring

Co-reporter:Peng Chen, Hai-Ming Wang, Guo-Jie Liu and Sean Xiao-An Zhang

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 19) pp:4456-4463

Publication Date(Web):05 Apr 2016

DOI:10.1039/C6OB00379F

Three molecular switches containing a fluorene ring were designed and synthesized. The introduction of the amino group substituted fluorene ring resulted in the target molecular switches having some optical properties in the near-infrared region. It was demonstrated that the N-substituents on the fluorene rings and the switch units both had great influence on the molecular switch optical properties including the absorption maximum, absorption intensity and fluorescence quantum yield. The open-ring forms IA and IIA showed obvious solvatochromic behaviour. The closed-ring forms IIB and IIIB showed obvious hydrochromic behaviour in MeCN/water binary solvent systems and acidichromic behaviour in MeCN solution with high reversibility. Especially, the distinct off–on fluorescence signal in the near-infrared region using the stimuli of acid means that the designed compounds have great potential application value in the field of biological sensing.

A stable aggregate system of silyl ether substituted quinacridone and its aggregation-state changes induced by fluoride-ions: inspiration for a dual guaranteed strategy for probe design

Co-reporter:Peng Chen, Guo-Jie Liu, Yuyang Wang and Sean Xiao-An Zhang

RSC Advances 2016 vol. 6(Issue 31) pp:25986-25991

Publication Date(Web):01 Mar 2016

DOI:10.1039/C6RA01487A

A sterically hindered silyl ether substituted quinacridone was successfully synthesized and its aggregation behaviors in different solvents were studied. It was demonstrated that the aggregate system of t-butyldiphenylsilyl ether substituted quinacridone in tetrahydrofuran was very stable and its aggregation-state could be tunable by fluoride-ion induced intermolecular force (e.g. hydrogen bonding and π–π stacking interactions) destructions and a chemical bond cleavage. The two aggregation-state changes of the system could be applied for a new dual guaranteed strategy for real-time naked-eye detection of fluoride-ions, which could provide assurance for both rapid responsive time and extraordinary selectivity.

Phosphine-catalyzed [4+2] annulations of α-aminonitriles with allenoates: Synthesis of functionalized tetrahydropyridines

Co-reporter:Hochol Jang;Wei Liu;Xiao’an Zhang Sean

Chemical Research in Chinese Universities 2016 Volume 32( Issue 3) pp:385-389

Publication Date(Web):2016 June

DOI:10.1007/s40242-016-5495-x

Phosphine-catalyzed [4+2] annulations of 2-(acetoxymethyl)buta-2,3-dienoates with α-aminonitriles have been developed, in which α-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-(acetoxymethyl)buta-2,3-dienoates as “C4 synthons” respectively. A number of α-aminonitriles could be successfully applied to giving multifunctional desired products using PPh3 as catalyst. This method provides a facile entry to access polysubstituted tetrahydropyridines bearing quaternary carbon centers. The possible reaction mechanism was also proposed.

Full-color tunable mechanofluorochromism and excitation-dependent emissions of single-arm extended tetraphenylethylenes

Co-reporter:Yi Wang, Ivan Zhang, Binhong Yu, Xiaofeng Fang, Xing Su, Yu-Mo Zhang, Ting Zhang, Bing Yang, Minjie Li and Sean Xiao-An Zhang

Journal of Materials Chemistry A 2015 vol. 3(Issue 47) pp:12328-12334

Publication Date(Web):04 Nov 2015

DOI:10.1039/C5TC02623G

We propose a new single-arm extension strategy on traditional tetraphenylethylene and successfully develop a new series of full-color (from ∼450 nm to ∼740 nm) tunable mechanofluorochromic materials. These materials exhibit efficient solid-state emission (quantum yield Φf > 10%) and high mechanofluorochromic contrast (wavelength shift from ∼50 nm to ∼100 nm). More importantly, we discover an unexpected excitation-dependent emission phenomenon of mechanofluorochromic materials and propose to utilize this new excitation-dependent emission behavior of materials to evaluate their mechanical-responsive performances more comprehensively. Finally, the unique feature of abundant emissions of mechanofluorochromic materials by changing the excitation light has shown application potential in dual channel anti-counterfeiting.

A new rhodamine based chemodosimeter for Ni2+ with high sensitivity and selectivity

Co-reporter:Ivan Zhang, Yi Wang, Chao Wan, Zhen Xing, Wen Li, Minjie Li and Sean Xiao-An Zhang

RSC Advances 2015 vol. 5(Issue 81) pp:66416-66419

Publication Date(Web):30 Jul 2015

DOI:10.1039/C5RA11737B

A new rhodamine derivative by modifying the ortho-position of the carboxylate in benzolate with amino pyridine has been developed, which exhibits high sensitivity and selectivity toward Ni2+ with a detection limit down to 4.6 ppb.

A single-molecule multicolor electrochromic device generated through medium engineering

Co-reporter:Yu-Mo Zhang, Xiaojun Wang, Weiran Zhang, Wen Li, Xiaofeng Fang, Bing Yang, Minjie Li and Sean Xiao-An Zhang

Light: Science & Applications 2015 4(2) pp:e249

Publication Date(Web):2015-02-01

DOI:10.1038/lsa.2015.22

Multicolor organic electrochromic materials are important for the generation of full-color devices. However, achieving multiple colors using a single-molecule material has proved challenging. In this study, a multicolor electrochromic prototype device is generated by integrating medium engineering/in situ ‘electro base’/laminated electrode technologies with the simple flying fish-shaped methyl ketone TM1. This multicolor electrochromic (green, blue and magenta) device is durable and has a high coloration efficiency (350 cm2 C−1), a fast switching time (50 ms) and superior reversibility. This study is a successful attempt to integrate solvatochromism and basochromism in an electronic display. This integration not only introduces a new avenue for color tuning, in addition to the structural design of the colorant, but will also inspire further developments in the tuning of many other properties by this medium engineering approach, such as conductance and the redox property, and thereby accelerate versatile applications in data recording, ultrathin flexible displays, and optical communication and sensing.

Dynamic Behavior of Molecular Switches in Crystal under Pressure and Its Reflection on Tactile Sensing

Co-reporter:Yi Wang; Xiao Tan; Yu-Mo Zhang; Shaoyin Zhu; Ivan Zhang; Binhong Yu; Kai Wang; Bing Yang; Minjie Li; Bo Zou

Journal of the American Chemical Society 2014 Volume 137(Issue 2) pp:931-939

Publication Date(Web):December 22, 2014

DOI:10.1021/ja511499p

Molecular switches have attracted increasing interest in the past decades, due to their broad applications in data storage, optical gating, smart windows, and so on. However, up till now, most of the molecular switches are operated in solutions or polymer blends with the stimuli of light, heat, and electric fields. Herein, we demonstrate the first pressure-controllable molecular switch of a benzo[1,3]oxazine OX-1 in crystal. Distinct from the light-triggered tautomerization between two optical states, applying hydrostatic pressure on the OX-1 crystal results in large-scale and continuous states across the whole visible light range (from ∼430 to ∼700 nm), which has not been achieved with other stimuli. Based on detailed and systematic control experiments and theoretical calculation, the preliminary requirements and mechanism of pressure-dependent tautomerization are fully discussed. The contributions of molecular tautomerization to the large-scale optical modulation are also stressed. Finally, the importance of studying pressure-responsive materials on understanding tactile sensing is also discussed and a possible mechanotransduction mode is proposed.

Reply to Comment on “Carbon Dots with Continuously Tunable Full-Color Emission and Their Application in Ratiometric pH Sensing”

Co-reporter:Minjie Li and Sean Xiao-An Zhang

Chemistry of Materials 2014 Volume 26(Issue 20) pp:6084

Publication Date(Web):October 1, 2014

DOI:10.1021/cm503256m

Carbon Dots with Continuously Tunable Full-Color Emission and Their Application in Ratiometric pH Sensing

Co-reporter:Hui Nie, Minjie Li, Quanshun Li, Shaojun Liang, Yingying Tan, Lan Sheng, Wei Shi, and Sean Xiao-An Zhang

Chemistry of Materials 2014 Volume 26(Issue 10) pp:3104

Publication Date(Web):April 22, 2014

DOI:10.1021/cm5003669

Two types of carbon dots (C dots) exhibiting respective excitation-independent blue emission and excitation-dependent full-color emissions have been synthesized via a mild one-pot process from chloroform and diethylamine. This new bottom-up synthetic strategy leads to highly stable crystalline C dots with tunable surface functionalities in high reproducibility. By detailed characterization and comparison of the two types of C dots, it is proved concretely that the surface functional groups, such as C═O and C═N, can efficiently introduce new energy levels for electron transitions and result in the continuously adjustable full-color emissions. A simplified energy level and electron transition diagram has been proposed to help understand how surface functional groups affect the emission properties. By taking advantage of the unique excitation-dependent full-color emissions, various new applications can be anticipated. Here, as an example, a ratiometric pH sensor using two emission wavelengths of the C dots as independent references has been constructed to improve the reliability and accuracy, and the pH sensor is applied to the measurement of intracellular pH values and cancer diagnosis.

Highly durable colour/emission switching of fluorescein in a thin film device using “electro-acid/base” as in situ stimuli

Co-reporter:Yu-Mo Zhang, Wen Li, Xiaojun Wang, Bing Yang, Minjie Li and Sean Xiao-An Zhang

Chemical Communications 2014 vol. 50(Issue 12) pp:1420-1422

Publication Date(Web):04 Sep 2013

DOI:10.1039/C3CC44924F

A radical ion from electroreduced p-benzoquinone (BQ) was introduced as a new source of convenient in situ base for colour/emission switching of fluorescein in thin film devices. The devices show excellent switchability and reversibility with no degradation during our extended switching test of 1500 cycles.

Bio-inspired enol-degradation for multipurpose oxygen sensing

Co-reporter:Yu-Mo Zhang, Xiaojun Wang, Wen Li, Weiran Zhang, Minjie Li and Sean Xiao-An Zhang

Chemical Communications 2014 vol. 50(Issue 88) pp:13477-13480

Publication Date(Web):11 Sep 2014

DOI:10.1039/C4CC05831C

Inspired by the enol-degradation of luciferin, a new oxygen sensor with oppositely changed color and fluorescence has been designed. This new reaction-based dual mode sensor can not only be used as a highly selective instant “fluorescence on” oxygen probe, but also as a freshness indicator of food or food materials by using its property of time-adjustable color fading.

Electrochromic Switching and Microkinetic Behaviour of Oxazine Derivatives and Their Applications

Co-reporter:Shaoyin Zhu;Minjie Li;Sicheng Tang;Yu-Mo Zhang;Bing Yang

European Journal of Organic Chemistry 2014 Volume 2014( Issue 6) pp:1227-1235

Publication Date(Web):

DOI:10.1002/ejoc.201301182

Abstract

Detailed electrochromic properties including the microkinetic switching behaviour of 2-nitro- (P1) and 2,8-dinitro-5a-[2-(4-dimethylaminophenyl)ethylene]-6,6-dimethyl-5a,6-dihydro-12H-indolo[2,1-b][1,3]benzooxazine (P2) were investigated in both solution and indium tin oxide (ITO) devices with a dual-wavelength time-dependent spectra monitoring method for the first time. These two oxazine derivatives displayed improved fatigue resistance and colour reversibility towards electrical stimulation compared with conventional spiropyran derivatives. A new electrochromic mechanism was proposed based on the experimental results and on quantum chemical calculations. Owing to an electron-withdrawing group para to the nitrogen of the indole fragment, P2 demonstrates better electro-driven reversibility of structural transformation between ring-open and ring-closed isomers than P1.

Morphology modulation and application of Au(I)–thiolate nanostructures

Co-reporter:Hui Nie, Minjie Li, Yajiao Hao, Xudong Wang, Sheng Gao, Peng Wang, Bo Ju and Sean Xiao-An Zhang

RSC Advances 2014 vol. 4(Issue 92) pp:50521-50528

Publication Date(Web):25 Sep 2014

DOI:10.1039/C4RA06500J

Controlled synthesis of Au(I)–3-mercaptopropionic acid (MPA) nanostructures with diverse morphologies, such as quasi-rectangular nanosheets, quasi-square nanosheets, nanobelts, nanostrings and nanochips, were successfully achieved. Regulating the morphology of Au(I)–MPA nanostructures was realized by reverse microemulsion, which not only has a confinement effect on the size but also directs their assembly into different morphologies. In addition, adjustment of the electrostatic interaction between ligands induces consecutive responses in Au(I)–Au(I) interaction and Au–S coordination, and also results in distinct morphology transformation. Taking advantage of the structural characteristics of the obtained Au(I)–MPA nanostructures, they are used as ideal precursors for the preparation of Au particles and photoluminescent Au clusters. This work not only provides effective strategies for the morphology regulation of coordination polymer nanostructures but also extends their application.

Cross polarization effect of donoracceptor group on a potential single-molecule transistor

Co-reporter:Yu-Mo. Zhang;Xiaojun Wang;Weiran Zhang;Wen Li;Bing Yang;Minjie Li

Journal of Physical Organic Chemistry 2014 Volume 27( Issue 11) pp:834-840

Publication Date(Web):

DOI:10.1002/poc.3345

Theoretical investigation of the polarization effect on a potential single-molecule transistor has been studied with density functional theory. 4,4′-(2-Amino-5-nitro-1,4-phenylene)bis(ethyne-2,1-diyl) dibenzenethiol (AN-OPE), containing a donor and an acceptor (D–A) crossed to its oligo(p-phenylene-ethynylene) (OPE) backbone, was used as a prototype for this study. Simulation results indicate that AN-OPE has a higher on/off ratio on conductance than OPE because of the larger polarization along the D–A direction. This high on/off ratio was proved by the 20 times variation in molecular charge, 15 times variation in bond lengths, 49 times variation in polarizability, 9 times variation in the rotation angles, and 13 times variation in the highest occupied molecular orbital–lowest unoccupied molecular orbital gaps under the same gate using B3LYP/6-31G (d, p). And results imply that conjugated molecules with a cross D–A structure could be a good direction for constructing a better single-molecule field-effect transistor. Copyright © 2014 John Wiley & Sons, Ltd.

Time-resolved monitoring of dynamic self-assembly of Au(I)-thiolate coordination polymers

Co-reporter:Hui Nie, Minjie Li, Yajiao Hao, Xudong Wang and Sean Xiao-An Zhang

Chemical Science 2013 vol. 4(Issue 4) pp:1852-1857

Publication Date(Web):14 Feb 2013

DOI:10.1039/C3SC22215B

Research interest in dynamic assemblies of coordination polymers (CPs) has been rising in recent years for the similarity with life systems in their self-adaptable morphologies and properties. However, monitoring of the assembly process and elucidating the nature for the morphological transformation are very challenging. Here, UV-Vis spectroscopy has been explored as a time-resolved method for monitoring the self-assembly of Au(I)–thiolate CPs in situ. Both step-wise and synergetic effects of the weak interactions in Au(I)–3-mercaptopropionic acid (MPA) CPs, such as H-bonding, coordination bonding, Au(I)–Au(I) interactions and static interactions have been found from the spectral fingerprints, which elucidated the driving forces for the unique morphological transformations from strings to lamellar structures. This work represents a breakthrough in that dynamic self-assembly behaviours can be explained by molecular interactions from molecular level evidences. Based on the spectral fingerprint–structure relationship the reversible and dynamic assembly of Au(I)–MPA CPs can be easily probed.

A new class of “electro-acid/base”-induced reversible methyl ketone colour switches

Co-reporter:Yu-Mo Zhang, Minjie Li, Wen Li, Zhiyuan Huang, Shaoyin Zhu, Bing Yang, Xiao-Chun Wang and Sean Xiao-An Zhang

Journal of Materials Chemistry A 2013 vol. 1(Issue 34) pp:5309-5314

Publication Date(Web):25 Jun 2013

DOI:10.1039/C3TC30769G

Methyl ketone has been designed as a switching unit for electrically addressable molecular colour switches. A newly proposed mechanism of “electro-acid/base” (radical ions)-induced intermolecular proton transfer for the colour switch is proven clearly by cyclic voltammetry (CV), X-ray photoelectron spectroscopy (XPS), infrared spectroscopy (IR) and in situ UV-Vis spectroscopy. A dramatic spectral absorption shift (about 291 nm) is observed during the switching, and blue, yellow and green colours are obtained by adjusting the substituents on the methyl ketone-bridged unit. The in situ “electro-acid/base” is far more convenient than the conventional chemical stimulus of acids or bases for the manipulation of the molecular switching properties. This new switching method and molecular structure manipulation will inspire and accelerate the further development of broad switching materials and applications in ultrathin flexible displays, etc.

Stress acidulated amphoteric molecules and mechanochromism via reversible intermolecular proton transfer

Co-reporter:Yi Wang, Minjie Li, Yumo Zhang, Jin Yang, Shaoyin Zhu, Lan Sheng, Xudong Wang, Bing Yang and Sean Xiao-An Zhang

Chemical Communications 2013 vol. 49(Issue 59) pp:6587-6589

Publication Date(Web):09 May 2013

DOI:10.1039/C3CC42747A

Stress has been proved to acidulate amphoteric molecules and promote an intermolecular proton transfer, which results in a significant absorption and emission change. The stress acidulated amphoteric molecules open a new avenue for developing mechanochromic materials and anticipate many broad applications such as stress/pressure sensors and rewritable media.

AIE (AIEE) and mechanofluorochromic performances of TPE-methoxylates: effects of single molecular conformations

Co-reporter:Qingkai Qi, Yifei Liu, Xiaofeng Fang, Yumo Zhang, Peng Chen, Yi Wang, Bing Yang, Bin Xu, Wenjing Tian and Sean Xiao-An Zhang

RSC Advances 2013 vol. 3(Issue 21) pp:7996-8002

Publication Date(Web):15 Mar 2013

DOI:10.1039/C3RA40734A

Two methoxy-substituted tetraphenylethylene (TPE) derivatives, tetra(4-methoxyphenyl)ethylene (TMOE) and tetra(3,4-dimethoxyphenyl)ethylene (TDMOE), were synthesized by McMurry reaction in high yields. The nearly centrosymmetric and natural propeller shape of TMOE and TDMOE excluded intermolecular effects, such as H or J-aggregation and π–π stacking, on their AIE (AIEE) and mechanofluorochromic performance. The crystal structures of TMOE and TDMOE, and theoretical calculations proved that their emission colours are determined by single molecular conjugation. These molecules were used to investigate pure conformational effects on molecular emissions. The spectral properties of these molecules in five environments of crystal(s), THF solution, THF–water binary solution, solidified THF and amorphous states, were investigated. The crystalline to amorphous phase transition by grinding resulted in good mechanofluorochromic performances with high quantum yields and distinguishable emission change, which was further explored as anti-counterfeiting inks on banknotes.

Hyperconjugation effect on fluorescence enhancement of biomimic disulfide substituted spirooxazine

Co-reporter:Shaoyin Zhu, Minjie Li, Yumo Zhang, Sicheng Tang, Jin Yang, Yi Wang, Lin Sun, Lan Sheng, Bing Yang and Sean Xiao-An Zhang

RSC Advances 2013 vol. 3(Issue 43) pp:19752-19755

Publication Date(Web):14 Aug 2013

DOI:10.1039/C3RA41487F

A remarkable 8-fold enhancement of fluorescence quantum efficiency was obtained for a novel spirooxazine with a disulfide substituent. X-ray analysis on the single crystal structure and quantum chemical calculations helped to confirm that the enhancement came from a spatial hyperconjugation between the disulfide unit with the charged conjugation bone of the molecule.

A TPE-oxazoline molecular switch with tunable multi-emission in both solution and solid state

Co-reporter:Qingkai Qi, Xiaofeng Fang, Yifei Liu, Peng Zhou, Yumo Zhang, Bing Yang, Wenjing Tian and Sean Xiao-An Zhang

RSC Advances 2013 vol. 3(Issue 38) pp:16986-16989

Publication Date(Web):24 Jul 2013

DOI:10.1039/C3RA43357A

A new multi-responsive tetraphenylethene functionalized oxazoline molecular switch (TPE-OX) was synthesized, which not only preserves isomerization and AIE properties, but also demonstrates synergistic effects, showing tunable multi-emission both in solution and in solid states.

Light-Triggered Molecular Level Self-Healing Spiropyran Thin Film

Co-reporter:Bingjie Yang;Juehuan Liu;Hongzhi Zheng

Chinese Journal of Chemistry 2013 Volume 31( Issue 12) pp:1483-1487

Publication Date(Web):

DOI:10.1002/cjoc.201300639

Abstract

Spiropyran thin film with capability of light-triggered molecular level self-healing has been successfully designed and fabricated by Langmuir-Blodgett technology. Various remarkable properties of thin film shrinkage or height increase or self-healing nano-defect recovery under different fabrication conditions have been observed. In addition, further evidence of the self-healing, which resulted from the movement of spiropyran molecules (such as "standing" "lie-down" and "tip-toes" etc.) on the substrate, has also been observed from the reversible contact angle change of the thin film.

Cover Picture: Light-Triggered Molecular Level Self-Healing Spiropyran Thin Film (Chin. J. Chem. 12/2013)

Co-reporter:Bingjie Yang;Juehuan Liu;Hongzhi Zheng

Chinese Journal of Chemistry 2013 Volume 31( Issue 12) pp:

Publication Date(Web):

DOI:10.1002/cjoc.201390029

A spirooxazine derivative as a highly sensitive cyanide sensor by means of UV-visible difference spectroscopy

Co-reporter:Shaoyin Zhu, Minjie Li, Lan Sheng, Peng Chen, Yumo Zhang and Sean Xiao-An Zhang

Analyst 2012 vol. 137(Issue 23) pp:5581-5585

Publication Date(Web):18 Sep 2012

DOI:10.1039/C2AN35867K

A spirooxazine derivative 2-nitro-5a-(2-(4-dimethylaminophenyl)-ethylene)-6,6-dimethyl-5a,6-dihydro-12H-indolo[2,1-b][1,3]benzooxazine (P1) was explored as a sensitive cyanide probe. Different from conventional spiropyrans, P1 avoided locating the 3H-indolium cation and the 4-nitrophenolate anion in the same conjugated structure, which enhanced the positive charge of 3H-indolium cation so that the sensitivity and reaction speed were improved highly. UV-visible difference spectroscopy using P1 detection solution as a timely reference improved the measurement accuracy, prevented the error caused by the inherent absorption change of P1 solution with time. This enabled the “positive-negative alternative absorption peaks” in difference spectrum to be used as a finger-print to distinguish whether the spectral change was caused by cyanide. Benefiting from the special design of the molecular structure and the strategy of difference spectroscopy, P1 showed high selectivity and sensitivity for CN−. A detection limit of 0.4 μM and a rate constant of 1.1 s−1 were achieved.

A methyl ketone bridged molecule as a multi-stimuli-responsive color switch for electrochromic devices

Co-reporter:Yu-Mo Zhang, Fuli Xie, Wen Li, Yuyang Wang, Weiran Zhang, Xiaojun Wang, Minjie Li and Sean Xiao-An Zhang

Journal of Materials Chemistry A 2016 - vol. 4(Issue 21) pp:NaN4667-4667

Publication Date(Web):2016/04/13

DOI:10.1039/C5TC04236D

Highly durable colour/emission switching of fluorescein in a thin film device using “electro-acid/base” as in situ stimuli

Co-reporter:Yu-Mo Zhang, Wen Li, Xiaojun Wang, Bing Yang, Minjie Li and Sean Xiao-An Zhang

Chemical Communications 2014 - vol. 50(Issue 12) pp:NaN1422-1422

Publication Date(Web):2013/09/04

DOI:10.1039/C3CC44924F

Bio-inspired enol-degradation for multipurpose oxygen sensing

Co-reporter:Yu-Mo Zhang, Xiaojun Wang, Wen Li, Weiran Zhang, Minjie Li and Sean Xiao-An Zhang

Chemical Communications 2014 - vol. 50(Issue 88) pp:NaN13480-13480

Publication Date(Web):2014/09/11

DOI:10.1039/C4CC05831C

Stress acidulated amphoteric molecules and mechanochromism via reversible intermolecular proton transfer

Co-reporter:Yi Wang, Minjie Li, Yumo Zhang, Jin Yang, Shaoyin Zhu, Lan Sheng, Xudong Wang, Bing Yang and Sean Xiao-An Zhang

Chemical Communications 2013 - vol. 49(Issue 59) pp:NaN6589-6589

Publication Date(Web):2013/05/09

DOI:10.1039/C3CC42747A

Time-resolved monitoring of dynamic self-assembly of Au(I)-thiolate coordination polymers

Co-reporter:Hui Nie, Minjie Li, Yajiao Hao, Xudong Wang and Sean Xiao-An Zhang

Chemical Science (2010-Present) 2013 - vol. 4(Issue 4) pp:NaN1857-1857

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