Modulation of physical properties of organic cocrystals by amino acid chirality

Wei Ji, Bin Xue, Santu Bera, Sarah Guerin, Linda J.W. Shimon, Qing Ma, Syed A.M. Tofail, Damien Thompson, Yi Cao, Wei Wang, Ehud Gazit*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

Amino acid chirality plays an important role in conveying directionality and specificity to their supramolecular organization. However, the impact of enantiopure and racemic amino acids on the favorable packing and macroscopic properties of organic cocrystals with nonchiral coformers is poorly understood. Herein, we performed a systematic study of the effect of chirality on the macroscopic properties of acetylated alanine (AcA) single crystals and cocrystals with a nonchiral photo-sensitive bipyridine derivative (BPE). Cocrystallization with BPE produced a marked morphology transition that improved the supramolecular chirality, thermal stability and mechanical strength of AcA crystals. The distinct supramolecular packing modes were analyzed by X-ray crystallography. The highest rigidity was observed for BPE/DL-AcA, while BPE/D-AcA and BPE/L-AcA crystals exhibited higher efficiency of photo-induced emission for fluorescent imprinting, as well as significantly higher piezoelectricity. This work provides a striking illustration that subtle differences in amino acid stereochemistry translate into tunable macroscopic properties of organic cocrystals for future applications in rigid solids, fluorescent imprinting, and energy harvesting.

Original languageEnglish
Pages (from-to)29-40
Number of pages12
JournalMaterials Today
Volume42
DOIs
StatePublished - 1 Jan 2021

Funding

FundersFunder number
DL-AcA
Higher
Horizon 2020 Framework Programme
European Research Council
Science Foundation Ireland15/CDA/3491, 12/RC/2275
National Natural Science Foundation of China11804148
Chinese Center for Disease Control and Prevention
Natural Science Foundation of Jiangsu ProvinceBK20180320
Horizon 2020694426
Fundamental Research Funds for the Central Universities020414380118
Irish Centre for High-End Computing

    Fingerprint

    Dive into the research topics of 'Modulation of physical properties of organic cocrystals by amino acid chirality'. Together they form a unique fingerprint.

    Cite this