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Intermolecular Chirality Modulation of Binaphthalene-Bridged Bisporphyrins With Chiral Diamines.

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.

SUBMITTER: Lu W

PROVIDER: S-EPMC7919525 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Intermolecular Chirality Modulation of Binaphthalene-Bridged Bisporphyrins With Chiral Diamines.

Lu Wenxin W Gong Lei L Su Chaorui C Wang Qibao Q Ling Qing Q Wang Peng P Qi Dongdong D Bian Yongzhong Y

Frontiers in chemistry 20210212

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 af ...[more]

PMID: 33659235

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