Huang Libing, Hu Chuanjiang, Wang Yong
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China.
Chem Asian J. 2024 Jul 15;19(14):e202400359. doi: 10.1002/asia.202400359. Epub 2024 Jun 19.
We designed and synthesized a ureido-linked zinc bisporphyrinate [Zn(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 [Zn(UBis)].
我们设计并合成了一种脲基连接的双卟啉锌化合物[Zn(UBis)]。圆二色光谱表明，这种双卟啉锌化合物无需衍生化就能感知手性羧酸的手性。我们的研究表明，连接基中的苯环与卟啉平面形成π-π相互作用，并且羧酸在主客体复合物中与锌配位。密度泛函理论计算表明，双卟啉采取“Z”形构型，并且脲基与羧酸形成氢键。π-π相互作用、配位相互作用和氢键相互作用的结合导致了[Zn(UBis)]的手性传感能力。
