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Ethynylated Triphenylamine Monoboronic acid Chemosensors: Experimental and Theoretical Studies

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Abstract

New ethynylated triphenylamine boronic acid sensors 1 and 2 were designed and the photophysical properties, as well as the binding with tartaric acid and mandelic acid were studied. We found the emission intensity of the sensors is sensitive to the polarity of the solvents and the emission of sensor 2 is sensitive to protic solvents. Theoretical calculations on the low-lying excited states of these sensors predicted d-PET effect. Experimental observations show either a-PET effect or no significant PET effect for the sensors. The sensitivity of the emission of the sensors toward solvent polarity is used to rationalize the observed emission intensity-pH profiles.

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Acknowledgements

We thank the NSFC (20642003, 40806042, 20634040 and 20972024), Ministry of Education (SRF for ROCS, SRFDP-200801410004 and NCET-08-0077), PCSIRT (IRT0711), State Key Laboratory of Fine Chemicals (KF0710 and KF0802), State Key Laboratory of Chemo/Biosensing and Chemometrics (2008009), the Education Department of Liaoning Province (2009 T015) and Dalian University of Technology (SFDUT07005 and 1000-893394) for financial support. We are grateful to RS (UK) and NSFC (China) for the Cost-Share program and the annual CASE symposium.

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116012, People’s Republic of China

    Lina Chi, Yubo Wu, Xin Zhang, Shaomin Ji, Jingyin Shao & Jianzhang Zhao

  2. Department of Chemistry, School of Chemical Engineering, Dalian University of Technology, Dalian, 116012, People’s Republic of China

    Huimin Guo

  3. Faculty of Chemistry, Sichuan University, Chengdu, 610064, People’s Republic of China

    Xin Wang

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  1. Lina Chi
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  2. Yubo Wu
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  3. Xin Zhang
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  6. Huimin Guo
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Correspondence to Huimin Guo or Jianzhang Zhao.

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pH titration curves and DFT/TDDFT calculation results of sensor 2.

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Chi, L., Wu, Y., Zhang, X. et al. Ethynylated Triphenylamine Monoboronic acid Chemosensors: Experimental and Theoretical Studies. J Fluoresc 20, 1255–1265 (2010). https://doi.org/10.1007/s10895-010-0677-2

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