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Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry
Author(s) -
Chen JinFa,
Yin Xiaodong,
Wang Bowen,
Zhang Kai,
Meng Guoyun,
Zhang Songhe,
Shi Yafei,
Wang Nan,
Wang Suning,
Chen Pangkuan
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001145
Subject(s) - enantiopure drug , enantioselective synthesis , luminescence , chirality (physics) , circular dichroism , intramolecular force , enantiomer , chromophore , steric effects , chemistry , solvatochromism , materials science , molecule , photochemistry , combinatorial chemistry , crystallography , stereochemistry , catalysis , organic chemistry , optoelectronics , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Abstract Enantiopure molecules based on macrocyclic architecture are unique for applications in enantioselective host‐guest recognition, chiral sensing and asymmetric catalysis. Taking advantage of the chiral transfer from the intrinsically planar chirality of pillar[5]arenes, we herein present an efficient and straightforward approach to achieve early examples of highly luminescent chiral systems ( P5NN and P5BN ). The optical resolution of their enantiomers has been carried out via preparative chiral HPLC, which was ascribed to the molecular functionalization of pillar[5]arenes with π‐conjugated, sterically bulky triarylamine (Ar 3 N) as an electron donor and triarylborane (Ar 3 B) as an acceptor. This crucial design enabled investigations of the chiroptical properties, including circular dichroism (CD) and circularly polarized luminescence (CPL) in the solid state. The intramolecular charge transfer (ICT) nature in P5BN afforded an interesting thermochromic shift of the emission over a wide temperature range.