Solvent influence on the photophysical properties of 4-methoxy-N-methyl-1,8-naphthalimide.
4-Methoxy-N-methyl-1,8-naphthalimide (1) exhibits considerable solvatochromism and its UV-vis spectral properties have been studied in several polar/non-polar and protic/aprotic solvents, as well as in ethanol-water mixtures. The results reveal a strong influence of the solvent's polarity and its hydrogen-bond donor (HBD) capability on the photophysical properties of 1. For binary ethanol/water mixtures, preferential solvation models describe the band shifts in the probe's visible absorption spectrum well, but they fail to describe the corresponding shifts of the emission maxima. Pseudolinear approximations between solvent composition and molecule's transition energies, E(T), can be used to study the composition of ethanol-water mixtures, simplifying the mathematical treatment for eventual analytical applications.
Departamento de Química, Faculdade de Filosofia Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Dos Bandeirantes 3900, CEP 14040-901, Ribeirão Preto, S.P., Brazil. demets@ffclrp.usp.br
Grégoire J-F
GJ
Demets
Eduardo R
ER
Triboni
Emiliano B
EB
Alvarez
Guilherme M
GM
Arantes
Pedro Berci
PB
Filho
Mário J
MJ
Politi
D000431:Ethanol / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D053644:Naphthalimides; D010777:Photochemistry; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry*
D007094:Imides; D009281:Naphthalenes; D053644:Naphthalimides; D012997:Solvents; D014867:Water; D000431:Ethanol; C508931:4-methoxy-N-methyl-1,8-naphthalimide