Intermolecular Chirality Modulation of Binaphthalene-Bridged Bisporphyrins With Chiral Diamines

Wenxin Lu; Lei Gong; Chaorui Su; Qibao Wang; Qing Ling; Peng Wang; Dongdong Qi; Yongzhong Bian

doi:10.3389/fchem.2020.611257

Intermolecular Chirality Modulation of Binaphthalene-Bridged Bisporphyrins With Chiral Diamines

Front Chem. 2021 Feb 12:8:611257. doi: 10.3389/fchem.2020.611257. eCollection 2020.

Authors

Wenxin Lu^{1

2}, Lei Gong², Chaorui Su², Qibao Wang¹, Qing Ling¹, Peng Wang¹, Dongdong Qi², Yongzhong Bian²

Affiliations

¹ College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao, 266590, China.
² Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing, China.

Abstract

A new pair of 2,2'-diamino-1,1'-binaphthyl linked porphyrin dimers, (R)-/(S)-H, were synthesized to study their supramolecular interactions with a pair of chiral diamines ((R)-/(S)-PPDA) by using UV-Vis absorption, fluorescence and NMR titrations. The spectroscopic titrations indicated that sandwich-type 1:1 complexes were formed at low guest concentration and then transformed to 1:2 open complexes at high guest concentration. The supramolecular interactions afforded sensitive circular dichroism responses, and the CD signs of the 1:1 complexes are decided by the stereostructure of chiral diamine guests. Moreover, due to the shortened linking units, (R)-/(S)-H show more sensitive and predicable CD response than the previously reported hosts (R)-/(S)-H1 and this can be reasonably explained by DFT molecular modeling. The present results suggest (R)-/(S)-H are promising for chiral optical sensing.

Keywords: CD spectroscopy; chiral optical sensor; chirality; diamine; fluorescence spectroscopy; porphyrin.