Frontiers in Chemistry (Feb 2021)

Intermolecular Chirality Modulation of Binaphthalene-Bridged Bisporphyrins With Chiral Diamines

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

DOI
https://doi.org/10.3389/fchem.2020.611257
Journal volume & issue
Vol. 8

Abstract

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A new pair of 2,2ʹ-diamino-1,1ʹ-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