Dinitriles bearing AIE-active moieties: Synthesis, E/Z isomerization, and fluorescence properties

Thiago Teixeira Tasso; Taniyuki Furuyama; Nagao Kobayashi

doi:10.1002/chem.201406128

Dinitriles bearing AIE-active moieties: Synthesis, E/Z isomerization, and fluorescence properties

Thiago Teixeira Tasso, Taniyuki Furuyama, Nagao Kobayashi

SCI - Chemistry

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

24 Citations (Scopus)

Abstract

Dinitriles bearing aggregation-induced emission (AIE)-active moieties [tetraphenylethylene (TPE) or diphenylphenanthrene (DPP)] were prepared. Compounds 4 (TPElinked) and 8 (DPP-linked) showed considerably redshifted emission resulting from their large Stokes shifts and also strong fluorescence in the aggregated and solid states. Pure E and Z stereoisomers of both dinitriles were easily separated, and their isomerization equilibria and fluorescence properties were investigated. In addition to their pronounced AIEE behavior, 4 and 8 also showed various reversible chromic responses to external stimuli, namely, solvato-, piezo-, vapo-, and thermochromism, which make them potential candidates for smart materials.

Original language	English
Pages (from-to)	4817-4824
Number of pages	8
Journal	Chemistry - A European Journal
Volume	21
Issue number	12
DOIs	https://doi.org/10.1002/chem.201406128
Publication status	Published - 2015 Mar 16

Keywords

Aggregation
Cyanides
Dyes/pigments
Fluorescence
Solvatochromism

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201406128

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title = "Dinitriles bearing AIE-active moieties: Synthesis, E/Z isomerization, and fluorescence properties",

abstract = "Dinitriles bearing aggregation-induced emission (AIE)-active moieties [tetraphenylethylene (TPE) or diphenylphenanthrene (DPP)] were prepared. Compounds 4 (TPElinked) and 8 (DPP-linked) showed considerably redshifted emission resulting from their large Stokes shifts and also strong fluorescence in the aggregated and solid states. Pure E and Z stereoisomers of both dinitriles were easily separated, and their isomerization equilibria and fluorescence properties were investigated. In addition to their pronounced AIEE behavior, 4 and 8 also showed various reversible chromic responses to external stimuli, namely, solvato-, piezo-, vapo-, and thermochromism, which make them potential candidates for smart materials.",

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T1 - Dinitriles bearing AIE-active moieties

T2 - Synthesis, E/Z isomerization, and fluorescence properties

AU - Tasso, Thiago Teixeira

AU - Furuyama, Taniyuki

AU - Kobayashi, Nagao

PY - 2015/3/16

Y1 - 2015/3/16

N2 - Dinitriles bearing aggregation-induced emission (AIE)-active moieties [tetraphenylethylene (TPE) or diphenylphenanthrene (DPP)] were prepared. Compounds 4 (TPElinked) and 8 (DPP-linked) showed considerably redshifted emission resulting from their large Stokes shifts and also strong fluorescence in the aggregated and solid states. Pure E and Z stereoisomers of both dinitriles were easily separated, and their isomerization equilibria and fluorescence properties were investigated. In addition to their pronounced AIEE behavior, 4 and 8 also showed various reversible chromic responses to external stimuli, namely, solvato-, piezo-, vapo-, and thermochromism, which make them potential candidates for smart materials.

AB - Dinitriles bearing aggregation-induced emission (AIE)-active moieties [tetraphenylethylene (TPE) or diphenylphenanthrene (DPP)] were prepared. Compounds 4 (TPElinked) and 8 (DPP-linked) showed considerably redshifted emission resulting from their large Stokes shifts and also strong fluorescence in the aggregated and solid states. Pure E and Z stereoisomers of both dinitriles were easily separated, and their isomerization equilibria and fluorescence properties were investigated. In addition to their pronounced AIEE behavior, 4 and 8 also showed various reversible chromic responses to external stimuli, namely, solvato-, piezo-, vapo-, and thermochromism, which make them potential candidates for smart materials.

KW - Aggregation

KW - Cyanides

KW - Dyes/pigments

KW - Fluorescence

KW - Solvatochromism

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Dinitriles bearing AIE-active moieties: Synthesis, E/Z isomerization, and fluorescence properties

Abstract

Keywords

ASJC Scopus subject areas

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