Aggregation-Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base

Chihiro Maeda; Shuichi Nomoto; Kazuto Takaishi; Tadashi Ema

doi:10.1002/chem.202001463

Aggregation-Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base

Chihiro Maeda, Shuichi Nomoto, Kazuto Takaishi, Tadashi Ema

School of Engineering

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

A variety of carbazolyl-appended Schiff bases were readily synthesized from 1-formylcarbazoles and aniline derivatives. Boron complexation of the resulting ligands allowed for facile preparation of new carbazole-based BODIPY analogues showing solid-state fluorescence. Furthermore, some dyes were converted into chiral compounds through the Et₂AlCl-mediated incorporation of a binaphthyl unit. The chiral dyes showed aggregation-induced fluorescence and circularly polarized luminescence (CPL) with the Φ_F and g_lum of up to 0.22 and −3.5×10⁻³, respectively, in the solid state. The solid-state fluorescence and CPL were well characterized by the crystal packing analyses and DFT calculations.

Original language	English
Pages (from-to)	13016-13021
Number of pages	6
Journal	Chemistry - A European Journal
Volume	26
Issue number	57
DOIs	https://doi.org/10.1002/chem.202001463
Publication status	Published - Oct 9 2020

Keywords

boron complexes
carbazoles
circularly polarized luminescence
dyes/pigments
solid-state fluorescence

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202001463

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title = "Aggregation-Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base",

abstract = "A variety of carbazolyl-appended Schiff bases were readily synthesized from 1-formylcarbazoles and aniline derivatives. Boron complexation of the resulting ligands allowed for facile preparation of new carbazole-based BODIPY analogues showing solid-state fluorescence. Furthermore, some dyes were converted into chiral compounds through the Et2AlCl-mediated incorporation of a binaphthyl unit. The chiral dyes showed aggregation-induced fluorescence and circularly polarized luminescence (CPL) with the ΦF and glum of up to 0.22 and −3.5×10−3, respectively, in the solid state. The solid-state fluorescence and CPL were well characterized by the crystal packing analyses and DFT calculations.",

keywords = "boron complexes, carbazoles, circularly polarized luminescence, dyes/pigments, solid-state fluorescence",

author = "Chihiro Maeda and Shuichi Nomoto and Kazuto Takaishi and Tadashi Ema",

note = "Funding Information: This work was supported by JSPS KAKENHI (Grant Number 18K05083, Tokuyama foundation Science Foundation, and Okayama Foundation for Science and Technology. We are grateful to A. Osuka, T. Tanaka, and M. Umetani for X‐ray diffraction analysis and fluorescence measurements, and to H. Yorimitsu for mass spectrometry measurements. ",

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doi = "10.1002/chem.202001463",

language = "English",

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T1 - Aggregation-Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base

AU - Maeda, Chihiro

AU - Nomoto, Shuichi

AU - Takaishi, Kazuto

AU - Ema, Tadashi

N1 - Funding Information: This work was supported by JSPS KAKENHI (Grant Number 18K05083, Tokuyama foundation Science Foundation, and Okayama Foundation for Science and Technology. We are grateful to A. Osuka, T. Tanaka, and M. Umetani for X‐ray diffraction analysis and fluorescence measurements, and to H. Yorimitsu for mass spectrometry measurements.

PY - 2020/10/9

Y1 - 2020/10/9

N2 - A variety of carbazolyl-appended Schiff bases were readily synthesized from 1-formylcarbazoles and aniline derivatives. Boron complexation of the resulting ligands allowed for facile preparation of new carbazole-based BODIPY analogues showing solid-state fluorescence. Furthermore, some dyes were converted into chiral compounds through the Et2AlCl-mediated incorporation of a binaphthyl unit. The chiral dyes showed aggregation-induced fluorescence and circularly polarized luminescence (CPL) with the ΦF and glum of up to 0.22 and −3.5×10−3, respectively, in the solid state. The solid-state fluorescence and CPL were well characterized by the crystal packing analyses and DFT calculations.

AB - A variety of carbazolyl-appended Schiff bases were readily synthesized from 1-formylcarbazoles and aniline derivatives. Boron complexation of the resulting ligands allowed for facile preparation of new carbazole-based BODIPY analogues showing solid-state fluorescence. Furthermore, some dyes were converted into chiral compounds through the Et2AlCl-mediated incorporation of a binaphthyl unit. The chiral dyes showed aggregation-induced fluorescence and circularly polarized luminescence (CPL) with the ΦF and glum of up to 0.22 and −3.5×10−3, respectively, in the solid state. The solid-state fluorescence and CPL were well characterized by the crystal packing analyses and DFT calculations.

KW - boron complexes

KW - carbazoles

KW - circularly polarized luminescence

KW - dyes/pigments

KW - solid-state fluorescence

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DO - 10.1002/chem.202001463

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SN - 0947-6539

VL - 26

SP - 13016

EP - 13021

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 57

ER -

Aggregation-Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base

Abstract

Keywords

ASJC Scopus subject areas

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