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Near infrared two-photon-excited and -emissive dyes based on a strapped excited-state intramolecular proton-transfer (ESIPT) scaffold

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Abstract

Fluorophores that can undergo excited-state intramolecular proton transfer (ESIPT) represent promising scaffolds for the design of compounds that show red-shifted fluorescence. Herein, we disclose new near infrared-emissive materials based on a dialkylamine-strapped 2,5-dithienylpyrrole as an ESIPT scaffold. The introduction of electron-accepting units to the terminal positions of this scaffold generates acceptor–π–donor–π–acceptor (A–π–D–π–A) type π-conjugated compounds. Following the ESIPT, the electron-donating ability of the core scaffold increases, which results in a substantially red-shifted emission in the NIR region, while increasing the oscillator strength. The electron-accepting units play a vital role to achieve intense and red-shifted emission from the ESIPT state. The strapped dialkylamine chain that forms an intramolecular hydrogen bond is also essential to induce the ESIPT. Moreover, an extended A–π–D–π–A skeleton enables two-photon excitation with the NIR light. One of the derivatives that satisfy these features, i.e., borylethenyl-substituted 5, exhibited an intense NIR emission in polar solvents such as acetone (λem = 708 nm, ΦF = 0.55) with a strong two-photon-absorption band in the NIR region.

Graphical abstract: Near infrared two-photon-excited and -emissive dyes based on a strapped excited-state intramolecular proton-transfer (ESIPT) scaffold

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Publication details

The article was received on 07 Jan 2018, accepted on 26 Jan 2018 and first published on 01 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00066B
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Near infrared two-photon-excited and -emissive dyes based on a strapped excited-state intramolecular proton-transfer (ESIPT) scaffold

    N. Suzuki, K. Suda, D. Yokogawa, H. Kitoh-Nishioka, S. Irle, A. Ando, L. M. G. Abegão, K. Kamada, A. Fukazawa and S. Yamaguchi, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC00066B

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