A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties

Heping Shi; Jinwei Yang; Xiuqing Dong; Li Fang; Chuan Dong; Martin M F Choi

doi:10.1016/j.synthmet.2013.07.013

A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties

Heping Shi^*, Jinwei Yang, Xiuqing Dong, Li Fang, Chuan Dong, Martin M F Choi

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

15 Citations (Scopus)

Abstract

A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F^-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutylammonium fluoride (Bu₄N⁺F^-) to form an adduct of (Bu₄N)⁺(BDDICZ·F)^-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.

Original language	English
Pages (from-to)	42-48
Number of pages	7
Journal	Synthetic Metals
Volume	179
DOIs	https://doi.org/10.1016/j.synthmet.2013.07.013
Publication status	Published - Sept 2013

Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Mechanics of Materials
Mechanical Engineering
Metals and Alloys
Materials Chemistry

User-Defined Keywords

Benzothiazole
Dimesitylboron
Donor-π-acceptor
Indolo[3,2-b]carbazole
Photophysical properties
Sensing properties

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10.1016/j.synthmet.2013.07.013

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@article{9286ab5f00704ed7a84307d54321efa5,

title = "A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties",

abstract = "A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutylammonium fluoride (Bu4N+F-) to form an adduct of (Bu4N)+(BDDICZ·F)-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.",

keywords = "Benzothiazole, Dimesitylboron, Donor-π-acceptor, Indolo[3,2-b]carbazole, Photophysical properties, Sensing properties",

author = "Heping Shi and Jinwei Yang and Xiuqing Dong and Li Fang and Chuan Dong and Choi, {Martin M F}",

note = "Funding Information: This work was supported by the Natural Science Foundation of Shanxi Province ( 2013011013-1 ), National Natural Science Foundation of China ( 21175086 ), Shanxi Scholarship Council of China ( 2012-006 ), Shanxi Science and Technology Department ( 20100321085 ), and Fund of Key Laboratory of Optoelectronic Materials Chemistry and Physics, Chinese Academy of Sciences ( 2008DP173016 ). The authors express their sincere thanks to the Advanced Computing Facilities of the Supercomputing Centre of Computer Network Information Centre of Chinese Academy of Sciences for all the theoretical calculations. ",

year = "2013",

month = sep,

doi = "10.1016/j.synthmet.2013.07.013",

language = "English",

volume = "179",

pages = "42--48",

journal = "Synthetic Metals",

issn = "0379-6779",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units

T2 - Synthesis, photophysical and sensing properties

AU - Shi, Heping

AU - Yang, Jinwei

AU - Dong, Xiuqing

AU - Fang, Li

AU - Dong, Chuan

AU - Choi, Martin M F

N1 - Funding Information: This work was supported by the Natural Science Foundation of Shanxi Province ( 2013011013-1 ), National Natural Science Foundation of China ( 21175086 ), Shanxi Scholarship Council of China ( 2012-006 ), Shanxi Science and Technology Department ( 20100321085 ), and Fund of Key Laboratory of Optoelectronic Materials Chemistry and Physics, Chinese Academy of Sciences ( 2008DP173016 ). The authors express their sincere thanks to the Advanced Computing Facilities of the Supercomputing Centre of Computer Network Information Centre of Chinese Academy of Sciences for all the theoretical calculations.

PY - 2013/9

Y1 - 2013/9

N2 - A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutylammonium fluoride (Bu4N+F-) to form an adduct of (Bu4N)+(BDDICZ·F)-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.

AB - A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutylammonium fluoride (Bu4N+F-) to form an adduct of (Bu4N)+(BDDICZ·F)-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.

KW - Benzothiazole

KW - Dimesitylboron

KW - Donor-π-acceptor

KW - Indolo[3,2-b]carbazole

KW - Photophysical properties

KW - Sensing properties

UR - http://www.scopus.com/inward/record.url?scp=84882434903&partnerID=8YFLogxK

U2 - 10.1016/j.synthmet.2013.07.013

DO - 10.1016/j.synthmet.2013.07.013

M3 - Journal article

AN - SCOPUS:84882434903

SN - 0379-6779

VL - 179

SP - 42

EP - 48

JO - Synthetic Metals

JF - Synthetic Metals

ER -

A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties

Abstract

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