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Inclusion as a driving force for the intramolecular charge transfer (ICT) fluorescence of p-(N,N-diphenylamino)benzoic acid methyl ester (DPABME) in α-cyclodextrin (α-CD) aqueous solution

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Abstract

A 1:1 inclusion complex between p-(N,N-diphenylamino)benzoic acid methyl ester (DPABME) molecule and α-cyclodextrin (α-CD) in aqueous solution is formed with a stabilization constant of ca. 45.65 ± 3.59 M−1 at 25 °C. The formation of the complex is accompanied by enhancement of the long wavelength fluorescence at 510 nm (attributed to intramolecular charge transfer (ICT) due to twisting) relative to the normal fluorescence at 420 nm. In water, the long-wavelength fluorescence is hidden under the red tail of the normal fluorescence band due to quenching by non-radiative transition. Inclusion by CD reduces quenching and thus constitutes a driving force for DPABME to emit at longer wavelength via ICT process.

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Acknowledgment

We would like to acknowledge Yarmouk University for financial support (grant no. 2007/14).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Yarmouk University, Irbid, 21163, Jordan

    Khader A. Al-Hassan, Na’il Saleh & Yaser A. Yousef

  2. Department of Chemistry, University of Sharjah, Sharjah, 27272, United Arab Emirates

    Ideisan I. Abu-Abdoun

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  1. Khader A. Al-Hassan
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  2. Na’il Saleh
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  3. Ideisan I. Abu-Abdoun
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  4. Yaser A. Yousef
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Correspondence to Khader A. Al-Hassan.

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Al-Hassan, K.A., Saleh, N., Abu-Abdoun, I.I. et al. Inclusion as a driving force for the intramolecular charge transfer (ICT) fluorescence of p-(N,N-diphenylamino)benzoic acid methyl ester (DPABME) in α-cyclodextrin (α-CD) aqueous solution. J Incl Phenom Macrocycl Chem 61, 361–365 (2008). https://doi.org/10.1007/s10847-008-9430-8

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