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Configurations dependent optical properties and acid susceptibility of azulene compounds

Abstract

We report the unique optical and protonation characteristics of azulene compounds with different molecular configurations, and demonstrate their potential application as acid sensor materials. The unique characteristic of azulene compound is its large dipole moment, and azulene derivatives with conjugation either along or orthogonally to the dipole direction of azulene were synthesized and their electronic and optical properties were studied. Our results showed that azulene with conjugation orthogonally to the dipole direction exhibits significantly optical properties change upon protonation due to strong intermolecular charge transfer. The low band gap absorption can reach up to mid-IR range, albeit at high acid doping concentration. On the other hand, conjugated azulenes along the dipole direction could be protonated easily even at very low acid concentration (ppm level), which is attributed to the co-planar structures upon protonation and their high proton affinity. Mechanism behind the discrepancy between the two configurations are elucidated and further supported by computer simulation. The application of azulene chromophore for chemical sensor with sensitivity at ppm level was also demonstrated in this work.

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Publication details

The article was received on 22 Feb 2018, accepted on 10 Apr 2018 and first published on 12 Apr 2018


Article type: Paper
DOI: 10.1039/C8TC00895G
Citation: J. Mater. Chem. C, 2018, Accepted Manuscript
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    Configurations dependent optical properties and acid susceptibility of azulene compounds

    T. Tang, T. T. Lin, F. Erden, F. Wang and C. He, J. Mater. Chem. C, 2018, Accepted Manuscript , DOI: 10.1039/C8TC00895G

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