Jump to main content
Jump to site search


A study of the competitive multiple hydrogen bonding effect and its associated excited-state proton transfer tautomerism

Author affiliations

Abstract

1,8-Dihydroxynaphthalene-2,7-dicarbaldehyde (DHDA) has been strategically designed and synthesized with the aim to study the competitive multiple hydrogen bonding (H-bonding) effect and the associated excited-state intramolecular proton transfer reaction (ESIPT). In nonpolar solvents such as cyclohexane, equilibrium exists between the two H-bonding isomers DHDA-23_OO and DHDA-23_OI, both of which possess double intramolecular H-bonds. In polar, aprotic solvents such as CH2Cl2, DHDA-23_OO becomes the predominant species. Due to various degrees of H-bond induced changes of electronic configuration each isomer reveals a distinct absorption feature and excited-state behavior, in which DHDA-23_OI in cyclohexane undergoes double ESIPT in a stepwise manner, giving the first and second proton-transfer tautomer emissions maximized at ∼500 nm and 660 nm, respectively. As for DHDA-23_OO both single and double ESIPT are prohibited, resulting in an intense normal 450 nm emission band. In a single crystal DHDA-23_OI is the dominant species, which undergoes excited state double proton transfer, giving intense emission bands at 530 nm and 650 nm. The mechanism associated with competitive multiple H-bonding energetics and ESIPT was underpinned by detailed spectroscopy/dynamics and computational approaches.

Graphical abstract: A study of the competitive multiple hydrogen bonding effect and its associated excited-state proton transfer tautomerism

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Jul 2017, accepted on 03 Oct 2017 and first published on 03 Oct 2017


Article type: Paper
DOI: 10.1039/C7CP05002J
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
  •   Request permissions

    A study of the competitive multiple hydrogen bonding effect and its associated excited-state proton transfer tautomerism

    Y. Chen, P. Wu, C. Peng, J. Shen, C. Tsai, W. Hu and P. Chou, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP05002J

Search articles by author

Spotlight

Advertisements