Chirality Sensing of Chiral Carboxylic Acids by a Ureido-linked Zinc Bisporphyrinate

Libing Huang; Chuanjiang Hu; Yong Wang

doi:10.1002/asia.202400359

Chirality Sensing of Chiral Carboxylic Acids by a Ureido-linked Zinc Bisporphyrinate

Chem Asian J. 2024 May 14:e202400359. doi: 10.1002/asia.202400359. Online ahead of print.

Authors

Libing Huang¹, Chuanjiang Hu², Yong Wang¹

Affiliations

¹ Soochow University, College of Chemistry, Chemical Engineering and Materials Science, CHINA.
² Soochow University, College of Chemistry, Chemical Engineering and Materials Science, 199 Ren-Ai Road, Dushu Lake Campus,Suzhou Industrial Park, 215123, Suzhou, CHINA.

PMID: 38744672
DOI: 10.1002/asia.202400359

Abstract

We designed and synthesized a ureido-linked zinc bisporphyrinate [Zn2(UBis)]. CD spectra show that this zinc bisporphyrinate has the ability to sense the chirality of chiral carboxylic acids without derivatization. Our studies suggest that the phenyl ring in the linker forms π-π interactions with porphyrin planes and that the carboxylic acid is coordinated to the zinc in the host-guest complex. DFT calculations show that the bisporphyrin adopts a "Z"-shaped configuration, and that the ureido group forms hydrogen bonds with carboxylic acids. The combination of π-π interactions, coordination interactions and hydrogen bonding interactions leads to the chirality sensing ability of [Zn2(UBis)].

Keywords: Bisporphyrin * Carboxylic Acid * Circular Dichroism * Ureido * Chirality Sensing.