A Strap Strategy for Construction of an Excited-State Intramolecular Proton Transfer (ESIPT) System with Dual Fluorescence

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-07, Vol.53 (31), p.8231-8235
Main Authors: Suzuki, Naoya, Fukazawa, Aiko, Nagura, Kazuhiko, Saito, Shohei, Kitoh-Nishioka, Hirotaka, Yokogawa, Daisuke, Irle, Stephan, Yamaguchi, Shigehiro
Format: Article
Language:English
Subjects:
boron
Chromophores
Emissivity
ESIPT
Excitation
Fluorescence
hydrogen bonds
Models, Molecular
Polarity
Protons
Solvents
Spectrometry, Fluorescence
Straps
Strategy
Terminals
π conjugation
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Summary: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. Hold on to the strap: A new type of excited‐state intramolecular proton transfer (ESIPT) chromophores has been developed by incorporation of an amine‐embedded alkyl strap into an emissive boryl‐substituted dithienylpyrrole skeleton. The product's dual fluorescence covers a wide range in the visible region depending on the solvent polarity. The zwitterionic ESIPT state is efficiently stabilized by the aminoalkyl strap and the terminal boryl groups.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201404867