Substituent Modulation for Highly Bright 9-Borafluorene Derivatives with Carbazole Pendant

Ya Li; Xing Chen; Wenying Zhang; Junzheng Zhang; Liang Xu; Yali Qiao; Kanglei Liu; Nan Wang; Bangkuan Chen; Xiaodong Yin

doi:10.1021/acs.orglett.1c02619

Substituent Modulation for Highly Bright 9-Borafluorene Derivatives with Carbazole Pendant

Ya Li
, Xing Chen
, Wenying Zhang
, Junzheng Zhang
, Liang Xu^*
, Yali Qiao
, Kanglei Liu
, Nan Wang
, Bangkuan Chen^*
, Xiaodong Yin^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

11 Citations (Scopus)

Abstract

A series of 3,6-di-tert-butyl carbazole-functionalized 9-borafluorene derivatives have been prepared with outstandingly strong photoluminescence with quantum yields up to ca. 100 and 94% for Mes*BF-pCz in solution and film, respectively. 1,3,5-Tris(trifluoromethyl)benzene (FMes)-substituted compounds exhibit enhanced Lewis acidity with coordination to weak nucleophiles like tetrahydrofuran, resulting in a long afterglow at low temperature. The large two-photon absorption cross-section of ca. 1103 GM for Mes*BF-pCz at 800 nm in CH2Cl2 indicated its potential application in bioimaging.

Original language	English
Pages (from-to)	7236-7241
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.1c02619
Publication status	Published - 17 Sept 2021

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10.1021/acs.orglett.1c02619

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title = "Substituent Modulation for Highly Bright 9-Borafluorene Derivatives with Carbazole Pendant",

abstract = "A series of 3,6-di-tert-butyl carbazole-functionalized 9-borafluorene derivatives have been prepared with outstandingly strong photoluminescence with quantum yields up to ca. 100 and 94\% for Mes*BF-pCz in solution and film, respectively. 1,3,5-Tris(trifluoromethyl)benzene (FMes)-substituted compounds exhibit enhanced Lewis acidity with coordination to weak nucleophiles like tetrahydrofuran, resulting in a long afterglow at low temperature. The large two-photon absorption cross-section of ca. 1103 GM for Mes*BF-pCz at 800 nm in CH2Cl2 indicated its potential application in bioimaging.",

author = "Ya Li and Xing Chen and Wenying Zhang and Junzheng Zhang and Liang Xu and Yali Qiao and Kanglei Liu and Nan Wang and Bangkuan Chen and Xiaodong Yin",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

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doi = "10.1021/acs.orglett.1c02619",

language = "English",

volume = "23",

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T1 - Substituent Modulation for Highly Bright 9-Borafluorene Derivatives with Carbazole Pendant

AU - Li, Ya

AU - Chen, Xing

AU - Zhang, Wenying

AU - Zhang, Junzheng

AU - Xu, Liang

AU - Qiao, Yali

AU - Liu, Kanglei

AU - Wang, Nan

AU - Chen, Bangkuan

AU - Yin, Xiaodong

PY - 2021/9/17

Y1 - 2021/9/17

N2 - A series of 3,6-di-tert-butyl carbazole-functionalized 9-borafluorene derivatives have been prepared with outstandingly strong photoluminescence with quantum yields up to ca. 100 and 94% for Mes*BF-pCz in solution and film, respectively. 1,3,5-Tris(trifluoromethyl)benzene (FMes)-substituted compounds exhibit enhanced Lewis acidity with coordination to weak nucleophiles like tetrahydrofuran, resulting in a long afterglow at low temperature. The large two-photon absorption cross-section of ca. 1103 GM for Mes*BF-pCz at 800 nm in CH2Cl2 indicated its potential application in bioimaging.

AB - A series of 3,6-di-tert-butyl carbazole-functionalized 9-borafluorene derivatives have been prepared with outstandingly strong photoluminescence with quantum yields up to ca. 100 and 94% for Mes*BF-pCz in solution and film, respectively. 1,3,5-Tris(trifluoromethyl)benzene (FMes)-substituted compounds exhibit enhanced Lewis acidity with coordination to weak nucleophiles like tetrahydrofuran, resulting in a long afterglow at low temperature. The large two-photon absorption cross-section of ca. 1103 GM for Mes*BF-pCz at 800 nm in CH2Cl2 indicated its potential application in bioimaging.

UR - https://www.scopus.com/pages/publications/85115176737

U2 - 10.1021/acs.orglett.1c02619

DO - 10.1021/acs.orglett.1c02619

M3 - Article

C2 - 34463516

AN - SCOPUS:85115176737

SN - 1523-7060

VL - 23

SP - 7236

EP - 7241

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Substituent Modulation for Highly Bright 9-Borafluorene Derivatives with Carbazole Pendant

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