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Molecules 2014, 19(5), 6415-6427; doi:10.3390/molecules19056415
Article

2,5-PRODAN Derivatives as Highly Sensitive Sensors of Low Solvent Acidity

, ,  and *
Received: 2 April 2014; in revised form: 8 May 2014 / Accepted: 12 May 2014 / Published: 20 May 2014
(This article belongs to the Special Issue Fluorescent Probes)
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Abstract: Two 5-acyl-2-dimethylaminonaphthalene derivatives, one with a propionyl group and the other with a fused cyclohexanone ring, are investigated as sensors of H-bond-donating ability in protic solvents of low solvent acidity. Their fluorescence is highly quenched in protic solvents, and the quenching order of magnitude is linearly related to the H-bond-donating ability of the solvent as quantified by the solvent acidity (SA) scale. As the solvent acidity increases from 0.15 to 0.40, the fluorescence for both is quenched by more than a factor of ten; thus, they are extremely sensitive sensors of the hydrogen-bond-donating ability in this weakly acidic range. Preferential solvation studies suggest that quenching occurs from a doubly H-bonded excited state.
Keywords: H-bonding; sensor; fluorescence; quenching H-bonding; sensor; fluorescence; quenching
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yoon, A.H.; Whitworth, L.C.; Wagner, J.D.; Abelt, C.J. 2,5-PRODAN Derivatives as Highly Sensitive Sensors of Low Solvent Acidity. Molecules 2014, 19, 6415-6427.

AMA Style

Yoon AH, Whitworth LC, Wagner JD, Abelt CJ. 2,5-PRODAN Derivatives as Highly Sensitive Sensors of Low Solvent Acidity. Molecules. 2014; 19(5):6415-6427.

Chicago/Turabian Style

Yoon, Alexandra H.; Whitworth, Laura C.; Wagner, Joel D.; Abelt, Christopher J. 2014. "2,5-PRODAN Derivatives as Highly Sensitive Sensors of Low Solvent Acidity." Molecules 19, no. 5: 6415-6427.


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