A strap strategy for construction of an excited-state intramolecular proton transfer (ESIPT) system with dual fluorescence

Naoya Suzuki; Aiko Fukazawa; Kazuhiko Nagura; Shohei Saito; Hirotaka Kitoh-Nishioka; Daisuke Yokogawa; Stephan Irle; Shigehiro Yamaguchi

doi:10.1002/anie.201404867

A strap strategy for construction of an excited-state intramolecular proton transfer (ESIPT) system with dual fluorescence

Naoya Suzuki
, Aiko Fukazawa
, Kazuhiko Nagura
, Shohei Saito
, Hirotaka Kitoh-Nishioka
, Daisuke Yokogawa
, Stephan Irle
, Shigehiro Yamaguchi

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

126 Scopus citations

Abstract

An amine-embedded flexible alkyl strap has been incorporated into an emissive boryl-substituted dithienylpyrrole skeleton as a new entity of excited-state intramolecular proton transfer (ESIPT) chromophores. The π-electron system shows a dual emission, which covers a wide range of the visible region depending on the solvent polarity. The incorporation of the aminoalkyl strap as well as the terminal boryl groups efficiently stabilize the zwitterionic excited-state species resulting from the ESIPT even in an aqueous medium.

Original language	English
Pages (from-to)	8231-8235
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	31
DOIs	https://doi.org/10.1002/anie.201404867
State	Published - Jul 28 2014
Externally published	Yes

Keywords

ESIPT
boron
fluorescence
hydrogen bonds
π conjugation

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10.1002/anie.201404867

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title = "A strap strategy for construction of an excited-state intramolecular proton transfer (ESIPT) system with dual fluorescence",

abstract = "An amine-embedded flexible alkyl strap has been incorporated into an emissive boryl-substituted dithienylpyrrole skeleton as a new entity of excited-state intramolecular proton transfer (ESIPT) chromophores. The π-electron system shows a dual emission, which covers a wide range of the visible region depending on the solvent polarity. The incorporation of the aminoalkyl strap as well as the terminal boryl groups efficiently stabilize the zwitterionic excited-state species resulting from the ESIPT even in an aqueous medium.",

keywords = "ESIPT, boron, fluorescence, hydrogen bonds, π conjugation",

author = "Naoya Suzuki and Aiko Fukazawa and Kazuhiko Nagura and Shohei Saito and Hirotaka Kitoh-Nishioka and Daisuke Yokogawa and Stephan Irle and Shigehiro Yamaguchi",

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AU - Suzuki, Naoya

AU - Fukazawa, Aiko

AU - Nagura, Kazuhiko

AU - Saito, Shohei

AU - Kitoh-Nishioka, Hirotaka

AU - Yokogawa, Daisuke

AU - Irle, Stephan

AU - Yamaguchi, Shigehiro

PY - 2014/7/28

Y1 - 2014/7/28

N2 - An amine-embedded flexible alkyl strap has been incorporated into an emissive boryl-substituted dithienylpyrrole skeleton as a new entity of excited-state intramolecular proton transfer (ESIPT) chromophores. The π-electron system shows a dual emission, which covers a wide range of the visible region depending on the solvent polarity. The incorporation of the aminoalkyl strap as well as the terminal boryl groups efficiently stabilize the zwitterionic excited-state species resulting from the ESIPT even in an aqueous medium.

AB - An amine-embedded flexible alkyl strap has been incorporated into an emissive boryl-substituted dithienylpyrrole skeleton as a new entity of excited-state intramolecular proton transfer (ESIPT) chromophores. The π-electron system shows a dual emission, which covers a wide range of the visible region depending on the solvent polarity. The incorporation of the aminoalkyl strap as well as the terminal boryl groups efficiently stabilize the zwitterionic excited-state species resulting from the ESIPT even in an aqueous medium.

KW - ESIPT

KW - boron

KW - fluorescence

KW - hydrogen bonds

KW - π conjugation

UR - https://www.scopus.com/pages/publications/84905368835

U2 - 10.1002/anie.201404867

DO - 10.1002/anie.201404867

M3 - Article

AN - SCOPUS:84905368835

SN - 1433-7851

VL - 53

SP - 8231

EP - 8235

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

A strap strategy for construction of an excited-state intramolecular proton transfer (ESIPT) system with dual fluorescence

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Keywords

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