Atropisomers of a series of zinc tetraphenyl porphyrins were synthesized and used as supramolecular receptors. Rotation around the porphyrin-meso phenyl bonds is restricted by installing ortho-chlorine substituents on the phenyl groups. The chlorine substituents allowed chromatographic separation of atropisomers, which did not interconvert at room temperature. The porphyrin meso phenyl groups were also equipped with phenol groups, which led to the formation of intramolecular H-bonds when the zinc porphyrins were bound to pyridine ligands equipped with ester or amide side arms. Binding of the pyridine ligands with the conformationally locked chloroporphyrins was compared with the corresponding unsubstituted porphyrins, which are more flexible. The association constants of 150 zinc porphyrin–pyridine complexes were measured in two different solvents, toluene and 1,1,2,2-tetrachloroethane (TCE). These association constants were then used to construct 120 chemical double mutant cycles to quantify the influence of chlorine substitution on the free energy of intramolecular H-bonds formed between the phenol side arms of the porphyrins and the ester or amide side arms of the pyridine ligands. Conformational restriction leads to increases in the stability of some complexes and decreases in the stability of others with variations in the free energy contribution due to intramolecular H-bonding of −5 to +6 kJ mol−1.

o-Benzenedisulfonimide (OBS) was demonstrated for the first time to be a safe, recyclable, and water-tolerant Brønsted acidic catalyst for the ring-opening polymerization (ROP) of δ-valerolactone and ε-caprolactone using benzyl alcohol as the initiator. The polymerizations proceeded to afford poly(δ-valerolactone) and poly(ε-caprolactone) with controlled molecular weights and narrow polydispersities. The kinetics and chain extension experiments were carried out to confirm the controlled/living fashion of the polymerizations. In addition, 1H NMR and MALDI-TOF MS measurements strongly indicated that the initiator residue was incorporated into the obtained polymers. Furthermore, well-defined poly(δ-valerolactone)-block-poly(ε-caprolactone) has been successfully synthesized via OBS-catalyzed ROP.

A bio-based polyol synthesized from lysine was reported to be an alternative to petroleum polyols for preparation of polyurethane. With the benefits of a high hydroxyl value and a low acid value, rigid polyurethane foams prepared from this polyol showed low density, high closed cell content, high compressive strength, and good thermal stability. Mechanistic studies of the synthesis of this polyol were also investigated.

The synthesis of a novel l-lysine-based polyol derivative and the potential and limitations of such polyols as an alternative to petroleum polyols are reported. The reaction mechanism for the formation of l-lysine-based polyols is also described. This novel class of l-lysine-based polyols with high hydroxyl values and no acid values can be used in rigid polyurethane foams instead of some petroleum polyols. The l-lysine-based rigid polyurethane foams have low density, high closed cell content, low thermal conductivity, and high compressive strength.

Imidodiphosphoric acid (IDPA) catalyzed ring-opening polymerization (ROP) of δ-valerolactone (δ-VL) and ε-caprolactone (ε-CL) with benzyl alcohol (BnOH) as the initiator in toluene at room temperature was investigated. The overall conversions of δ-VL and ε-CL to poly(δ-valerolactone) (PVL) and poly(ε-caprolactone) (PCL), respectively, were more than 90%. Experimental results indicated the living nature of the polymerizations. The polymerization reactions with different monomer-to-initiator ratios proceeded homogeneously to afford PVL and PCL with controlled molecular weight and narrow polydispersities. 1H NMR and MALDI-TOF MS measurements demonstrated the quantitative incorporation of the initiator in the polymer chains. The controlled/living character of the polymerization was examined thoroughly by the kinetics and chain extension experiments, indicating that the IDPA-catalyzed ROPs of δ-VL and ε-CL proceeded through a living mechanism.

In the study, the epoxidation process of soybean oil by microflow system (MFS) was investigated. With formic acid as oxygen carrier and EDTA-2Na as stabilizer, the optimal result (epoxidized soybean oil (ESO) with an epoxy number (EN) of 7.3) was obtained in such conditions: temperature 75 °C, H2SO4 concentration 3%, EDTA-2Na dosage 3%, residence time 6.7 min, ratio of formic acid to hydrogen peroxide 1:1, and H2O2 to double bond molar ratio 8:1.

A novel protocol based on size-exclusion chromatography (SEC) and MS was established to accelerate dynamic combinatorial chemistry (DCC) in this study. By isolating ligand–target adducts from the dynamic combinatorial library (DCL), ligands could be identified directly by MS after denaturation. Three new inhibitors for lysozyme were discovered by this SEC–MS protocol in a case study. Km Data for these new inhibitors was also determined.

Atropisomers of a series of zinc tetraphenyl porphyrins were synthesized and used as supramolecular receptors. Rotation around the porphyrin-meso phenyl bonds is restricted by installing ortho-chlorine substituents on the phenyl groups. The chlorine substituents allowed chromatographic separation of atropisomers, which did not interconvert at room temperature. The porphyrin meso phenyl groups were also equipped with phenol groups, which led to the formation of intramolecular H-bonds when the zinc porphyrins were bound to pyridine ligands equipped with ester or amide side arms. Binding of the pyridine ligands with the conformationally locked chloroporphyrins was compared with the corresponding unsubstituted porphyrins, which are more flexible. The association constants of 150 zinc porphyrin–pyridine complexes were measured in two different solvents, toluene and 1,1,2,2-tetrachloroethane (TCE). These association constants were then used to construct 120 chemical double mutant cycles to quantify the influence of chlorine substitution on the free energy of intramolecular H-bonds formed between the phenol side arms of the porphyrins and the ester or amide side arms of the pyridine ligands. Conformational restriction leads to increases in the stability of some complexes and decreases in the stability of others with variations in the free energy contribution due to intramolecular H-bonding of −5 to +6 kJ mol−1.