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Issue 30, 2017
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Tuning the strength of intramolecular charge-transfer of triene-based nonlinear optical dyes for electro-optics and optofluidic lasers

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Abstract

Organic conjugated dyes have received extensive attention due to their broad applications in nonlinear optics and light-emitting and fluorescent sensors. Herein, we report the two-step synthesis of donor–acceptor dyes with triene-conjugated bridges. Via Vilsmeier formylation and Knoevenagel condensation, the dyes 1–4 with respectively varied electron-withdrawing moieties were successfully synthesized with high yields in short duration times. Photophysical properties showed gradually enhanced intramolecular charge-transfer (ICT) strength from dye 1 to dye 4 and diverse absorption and fluorescence properties. This structure–property tuning ensured their different applications in optofluidic lasers and nonlinear optics. Moreover, an optofluidic laser obtained using dye 1 in toluene as the gain material was demonstrated. Narrow linewidth (1.6 nm) of the optofluidic laser (peak wavelength: 610 nm) with a threshold of 94.2 μJ mm−2 was obtained. In electro-optic (EO) activities, four dyes in guest–host EO films showed the step-up EO coefficients from dye 1 (3 pm V−1) to dye 4 (76 pm V−1). This trend was in accordance with the results of ICT energy gap and DFT calculations, and it showed the effective tuning of structure–property relationship for electro-optics. The facile synthesis of NLO dyes, fine-tuning of their intramolecular charge-transfer, as well as the experimental demonstration in nonlinear optics and optofluidic lasers indicated their significant applications in organic photonic devices.

Graphical abstract: Tuning the strength of intramolecular charge-transfer of triene-based nonlinear optical dyes for electro-optics and optofluidic lasers

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Publication details

The article was received on 05 Mar 2017, accepted on 30 Jun 2017 and first published on 03 Jul 2017


Article type: Paper
DOI: 10.1039/C7TC00958E
Citation: J. Mater. Chem. C, 2017,5, 7472-7478
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    Tuning the strength of intramolecular charge-transfer of triene-based nonlinear optical dyes for electro-optics and optofluidic lasers

    J. Wu, W. Wang, C. Gong, Q. Li, Z. Li, G. Deng, X. Zhang, K. Chen, Y. Gong and K. S. Chiang, J. Mater. Chem. C, 2017, 5, 7472
    DOI: 10.1039/C7TC00958E

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