Macrocyclic bisbinaphthyl fluorophores and their acyclic analogues: signal amplification and chiral recognition

The Journal of Organic Chemistry
Zi-Bo LiLin Pu

Abstract

A series of optically active macrocyclic and acyclic bisbinaphthyls have been synthesized and characterized. The structure of one of the bisbinaphthyl macrocycles has been established by a single-crystal X-ray analysis. The UV and fluorescence spectra of these chiral compounds in various solvents and at different concentrations are studied. Formation of excimers is observed for the macrocyclic bisbinaphthyl compounds. Introduction of conjugated substituents to the 6,6'-positions of the binaphthyl units in the macrocycles leads to greatly amplified fluorescence signals. Using the 6,6'-substituted bisbinaphthyl macrocycles in place of the unsubstituted macrocycles allows a 2 orders of magnitude reduction in the sensor concentration for the fluorescence measurements. These macrocycles have exhibited highly enantioselective fluorescent enhancements in the presence of chiral alpha-hydroxycarboxylic acids and N-protected alpha-amino acids. They are useful as fluorescent sensors for chiral recognition. The macrocycles show much greater enantioselectivity in the substrate recognition than their acyclic analogues.

References

Nov 7, 2001·Chemistry : a European Journal·J C OstrowskiG C Bazan
Feb 20, 2002·Chemical Reviews·Xian Xin ZhangReed M. Izatt

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Citations

Jun 13, 2008·Journal of Fluorescence·Xiao-Huan HuangZhi-Hong Chen
Aug 13, 2011·Accounts of Chemical Research·Lin Pu
Sep 23, 2016·Journal of the American Chemical Society·Qi-Wei ZhangHe Tian
Aug 11, 2007·Bioorganic & Medicinal Chemistry Letters·Perumal RajakumarNarayanasamy Mathivanan
Feb 28, 2015·Chemical Communications : Chem Comm·Ali AkdenizPavel Anzenbacher
Jun 5, 2010·Organic & Biomolecular Chemistry·Marco CaricatoDario Pasini
Jul 12, 2011·Organic & Biomolecular Chemistry·Xia YangYixiang Cheng
Jan 12, 2010·Chemical Communications : Chem Comm·Sunderraman SambasivanKyo Han Ahn
Oct 26, 2016·Chemistry : a European Journal·Dawid LichosytJanusz Jurczak
Apr 30, 2008·The Journal of Organic Chemistry·Carmine ColucciniDario Pasini
Jun 9, 2021·Luminescence : the Journal of Biological and Chemical Luminescence·Hiroki TokunagaMakoto Miyasaka
Oct 26, 2018·The Journal of Organic Chemistry·Frescilia Octa-SmolinJochen Niemeyer
Feb 7, 2014·Chemical Reviews·Xin ZhangJuyoung Yoon

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