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CAS: 146054-12-8
MF: C20H9BN2OF2
MW: 342.10606
Synonyms:

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Weijiang He

Nanjing University
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Yan Zhang

Nanjing University
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Kothandam Krishnamoorthy

CSIR-Network of Institutes for Solar Energy
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Co-reporter: Saumya Singh, Vijay Venugopalan and Kothandam Krishnamoorthy  
pp: 13376-13382
Publication Date(Web):22 Apr 2014
DOI: 10.1039/C4CP01098A
Judiciously chosen side chains of conjugated molecules have a positive impact on charge transport properties when used as the active material in organic electronic devices. Amongst the side chains, oligoethylene glycols (OEGs) have been relatively unexplored due to their hydrophilic nature. OEGs also affect the smooth film formation of conjugated molecules, which preclude device fabrication. However, X-ray diffraction studies have shown that OEGs facilitate intermolecular contact, which is a desirable property for the fabrication of organic electronic devices. Thus the challenge is to design and synthesize organic solvent soluble and uniform film forming conjugated molecules with OEG side chains. We have designed and synthesized conjugated small molecules (CSMs) comprising BODIPY as acceptor and triphenylamine as donor with an OEG side chain. This molecule forms smooth films when processed from organic solvents. In order to understand the impact of the OEG side chain, we have also synthesized alkyl chain analogs. All the molecules exhibit exactly the same HOMO and LUMO energy levels, but the packing in the solid state is different. CSM with methyl side chains exhibit an inter planar distance of 4.15 Å. Contrary to this, the OEG side chain containing CSM showed an inter planar spacing of 4.30 Å, which is 0.2 Å less than the alkyl side chain comprising CSMs. Please note that the length of the hydrophobic and hydrophilic side chains is the same. Interestingly, the OEG side chain comprising CSM showed two orders of higher hole carrier mobilities compared to all the other derivatives. The same molecule also showed an extremely low threshold voltage of −0.27 V indicating the OEG side chains' favourable interaction between substrate as well as between molecules.
Co-reporter: Saumya Singh, Vijay Venugopalan and Kothandam Krishnamoorthy
pp: NaN13382-13382
Publication Date(Web):2014/04/22
DOI: 10.1039/C4CP01098A
Judiciously chosen side chains of conjugated molecules have a positive impact on charge transport properties when used as the active material in organic electronic devices. Amongst the side chains, oligoethylene glycols (OEGs) have been relatively unexplored due to their hydrophilic nature. OEGs also affect the smooth film formation of conjugated molecules, which preclude device fabrication. However, X-ray diffraction studies have shown that OEGs facilitate intermolecular contact, which is a desirable property for the fabrication of organic electronic devices. Thus the challenge is to design and synthesize organic solvent soluble and uniform film forming conjugated molecules with OEG side chains. We have designed and synthesized conjugated small molecules (CSMs) comprising BODIPY as acceptor and triphenylamine as donor with an OEG side chain. This molecule forms smooth films when processed from organic solvents. In order to understand the impact of the OEG side chain, we have also synthesized alkyl chain analogs. All the molecules exhibit exactly the same HOMO and LUMO energy levels, but the packing in the solid state is different. CSM with methyl side chains exhibit an inter planar distance of 4.15 Å. Contrary to this, the OEG side chain containing CSM showed an inter planar spacing of 4.30 Å, which is 0.2 Å less than the alkyl side chain comprising CSMs. Please note that the length of the hydrophobic and hydrophilic side chains is the same. Interestingly, the OEG side chain comprising CSM showed two orders of higher hole carrier mobilities compared to all the other derivatives. The same molecule also showed an extremely low threshold voltage of −0.27 V indicating the OEG side chains' favourable interaction between substrate as well as between molecules.

Dong Xue

Shaanxi Normal University
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Jia-hai Ye

Nanjing University of Science and Technology
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Tao Wang

Shaanxi Normal University
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Engin U. Akkaya

Bilkent University
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Co-reporter: Ilke Simsek Turan;Fatma Pir Cakmak;Deniz Cansen Yildirim;Rengul Cetin-Atalay;Dr. Engin U. Akkaya
pp: 16088-16092
Publication Date(Web):
DOI: 10.1002/chem.201405450

Abstract

Enhanced spatiotemporal selectivity in photonic sensitization of dissolved molecular oxygen is an important target for improving the potential and the practical applications of photodynamic therapy. Considering the high intracellular glutathione concentrations within cancer cells, a series of BODIPY-based sensitizers that can generate cytotoxic singlet oxygen only after glutathione-mediated cleavage of the electron-sink module were designed and synthesized. Cell culture studies not only validate our design, but also suggest an additional role for the relatively hydrophobic quencher module in the internalization of the photosensitizer.

Chao Wang

Shaanxi Normal University
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