Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self‐Assemblies
| Autor: | Li Yang, Minggao Qin, Xiaoqiu Dou, Chao Xing, Changli Zhao, Yaqian Zhang, Chuanliang Feng |
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| Rok vydání: | 2021 |
| Předmět: |
inorganic chemicals
Supramolecular chirality Dipeptide 010405 organic chemistry organic chemicals Organic Chemistry technology industry and agriculture Absolute configuration Supramolecular chemistry General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Self-assembly Diphenylalanine Enantiomer Chirality (chemistry) |
| Zdroj: | Chemistry – A European Journal. 27:3119-3129 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202004533 |
| Popis: | Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series of C2 -symmetrical dipeptide-based derivatives bearing various amino acid sequences and different chiralities are designed and synthesized. The transcription and amplification of molecular chirality to supramolecular assemblies are achieved. The results show that supramolecular chirality is only determined by the amino acid adjacent to the benzene core, irrespective of the absolute configuration of the C-terminal amino acid. In addition, molecular chirality also has a significant influence on the gelation behavior. For the diphenylalanine-based gelators, the homochiral gelators can be gelled through a conventional heating-cooling process, whereas heterochiral gelators form translucent stable gels under sonication. The racemic gels possess higher mechanical properties than those of the pure enantiomers. All of these results contribute to an increasing knowledge over control of the generation of specific chiral supramolecular structures and the development of new optimized strategies to achieve functional supramolecular organogels through heterochiral and racemic systems. |
| Databáze: | OpenAIRE |
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