Intramolecular donor-acceptor systems. Part 8. Solvent and substituent effects on the fluorescence emission of 6-N-methyl-N-phenylamino-2-naphthalenesulfon-N,N-dimethylamides

Edward M. Kosower*, Hannah Kanety

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The dual fluorescence (emissions from S1,np and S1,ct states) of N-phenylaminonaph-thalenesulfonate (ANS) systems is briefly reviewed. The 6-N-methyl-N-phenylamino-2-naphthalenesulfon-N,N-dimethylamides also exhibit dual fluorescence, as shown by plots of emission energy and ΦF against the solvent polarity parameter, ET(30). The solvent polarities, for which appearance of S1,ct emission marks the occurrence of an intramolecular electron transfer (i.e.t.) process, are appreciably lower than those of the corresponding sulfonates. The fluorescence of the dimethylamides exhibits a high sensitivity to substituent change, the apparent Hammett ρ{variant} value being ca. -13 for unsubstituted dimethylamide and -33 for N-methyl-substituted dimethylamide. The N,N-dimethylamides are particularly suitable for the investigation of the rates and mechanisms of intramolecular electron-transfer processes by picosecond and nanosecond pulse techniques.

Original languageEnglish
Pages (from-to)259-267
Number of pages9
JournalJournal of Molecular Structure
Volume84
Issue number3-4
DOIs
StatePublished - Oct 1982

Fingerprint

Dive into the research topics of 'Intramolecular donor-acceptor systems. Part 8. Solvent and substituent effects on the fluorescence emission of 6-N-methyl-N-phenylamino-2-naphthalenesulfon-N,N-dimethylamides'. Together they form a unique fingerprint.

Cite this