Spectroscopic study of excited state intramolecular charge transfer in ethyl ester of N,N′-Dimethylaminonaphthyl-(acrylic)-acid

Spectroscopic and theoretical evidence for the photoinduced twisted intramolecular charge transfer state formation in N,N-dimethylaminonaphthyl-(acrylo)-nitrile

“…The possible hydrogen-bonded clusters with polar protic solvents are shown in Scheme 2. The spectral characteristics are found to be similar to that of recently studied molecules MDMANA and EDMANA [33,34]. Table 1 Spectroscopic parameters of N,N-dimethylaminonaphthyl-(acrylo)-nitrile (DMANAN) obtained from band maxima of absorption and emission spectra…”

“…We have tried to explore the possibility of ICT process in naphthalene ring-containing systems for which there are very few examples [31,32]. Very recently, we have investigated donor-acceptor excited state CT reaction in naphthalene systems such as methyl ester of N,N-dimethylaminonaphthyl-(acrylic)-acid (MDMANA) and ethyl ester of N,N-dimethylaminonaphthyl-(acrylic)-acid (EDMANA) [33,34]. The title molecule has been synthesized, and the absorption and fluorescence spectroscopy have been used to study its photophysical behaviour.…”

Hydrogen‐Bonding Effects on Intramolecular Charge Transfer

“…ICT-state fluorescence was observed in solution phase by further solvation so that the amino site complex could absorb light. Although a few others [65,66] supported the Cazeau hypothesis, no clear unambiguous evidence was provided to substantiate the hypothesis. For instance, the twisted intramolecular charge transfer emission of ethyl and methyl esters of N, N-dimethylaminonaphthyl-(acrylic)-acid in polar protic solvents was reported to vary linearly with the hydrogen-bonding parameter a [65,66].…”

“…Although a few others [65,66] supported the Cazeau hypothesis, no clear unambiguous evidence was provided to substantiate the hypothesis. For instance, the twisted intramolecular charge transfer emission of ethyl and methyl esters of N, N-dimethylaminonaphthyl-(acrylic)-acid in polar protic solvents was reported to vary linearly with the hydrogen-bonding parameter a [65,66]. The authors referred to the Cazeau model of the ground-state tetragonal arrangement of the amine side owing to the formation of a hydrogen bond with protic solvents, which is supposed to favour the TICT process.…”

Solute–Solvent Hydrogen Bond Formation in the Excited State. Experimental and Theoretical Evidence

“…For (E)-3-(4-methylamino-phenyl)-acrylic acid ethyl ester (MAPAEE in Figure 4.9), three possible positions for H-bond formation in protic solvents can be assumed: two sites involving the oxygen atoms of the acceptor and one implicating the lone pair of the nitrogen which can fix a hydrogen from the solvent [83]. In non-polar solvents Similarly, the methyl ester of N,N-dimethylaminonaphthyl-(acrylic)-acid (MDMANA) also presents dual emission in polar and protic solvents and a single fluorescence band in non-polar solvents [113,114]. The LW band shifts from 461 nm in CCl 4 to 521 nm in water and was ascribed to a CT band.…”