TY - JOUR
T1 - 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
AU - Kosower, Edward M.
AU - Kanety, Hannah
PY - 1982/10
Y1 - 1982/10
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=49049143387&partnerID=8YFLogxK
U2 - 10.1016/0022-2860(82)85259-9
DO - 10.1016/0022-2860(82)85259-9
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AN - SCOPUS:49049143387
SN - 0022-2860
VL - 84
SP - 259
EP - 267
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
IS - 3-4
ER -