Next Article in Journal
Antiprotozoal Activity of Achillea ptarmica (Asteraceae) and Its Main Alkamide Constituents
Next Article in Special Issue
Organic Liquids-Responsive β-Cyclodextrin-Functionalized Graphene-Based Fluorescence Probe: Label-Free Selective Detection of Tetrahydrofuran
Previous Article in Journal
CopA3 Peptide Prevents Ultraviolet-Induced Inhibition of Type-I Procollagen and Induction of Matrix Metalloproteinase-1 in Human Skin Fibroblasts
Previous Article in Special Issue
Turn-on Type Chemical Sensing of Vitamin K4 by Fluorene Dendrimers with Naphthalene Segments
Article Menu

Export Article

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

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

Department of Chemistry, College of William and Mary, Williamsburg, VA 23187-8795, USA
Author to whom correspondence should be addressed.
Received: 2 April 2014 / Revised: 8 May 2014 / Accepted: 12 May 2014 / Published: 20 May 2014
(This article belongs to the Special Issue Fluorescent Probes)
View Full-Text   |   Download PDF [1061 KB, uploaded 18 June 2014]   |  


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 (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top