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1 December 2004 Spectroscopic Properties of Various Quinolone Antibiotics in Aqueous–organic Solvent Mixtures
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Abstract

The spectroscopic properties of enoxacin (ENO), oxolinic acid (OXO) and nalidixic acid (NAL) were studied in various H2O–CH3OH and H2O–CH3CN mixed solvents because these solvents were thought to behave as a biological mimetic system. ENO has piperazinyl group, but OXO and NAL do not have this substituent. The fluorescence emission spectra of ENO were very sensitive to the composition of the solvents. In the Lippert–Mataga analysis of the steady-state fluorescence data, clear reverse solvatochromism was exhibited for ENO in both mixed solvents. This observation can be explained using the excited state twisted intramolecular charge transfer (TICT) from the nitrogen of the piperazinyl group to the keto oxygen. Theoretical calculations further support this observation. The nonradiative and radiative rate constants of these molecules were analyzed as a function of dipolarity–polarizability (π*) and hydrogen bond donor acidity (α) of the mixed solvents. These results for ENO were consistent with the suggested mechanism of the TICT very well. The influence of bulk dielectric effect was more significant relative to the specific hydrogen bonding interactions. The emission spectra of OXO and NAL do not exhibit any characteristic responses to the properties of the solvent.

Hyoung-Ryun Park, Chu-Ha Oh, Hyeong-Chul Lee, Sam Ryong Lim, Kiyull Yang, and Ki-Min Bark "Spectroscopic Properties of Various Quinolone Antibiotics in Aqueous–organic Solvent Mixtures," Photochemistry and Photobiology 80(3), 554-564, (1 December 2004). https://doi.org/10.1562/0031-8655(2004)080<0554:SPOVQA>2.0.CO;2
Received: 23 April 2004; Accepted: 1 July 2004; Published: 1 December 2004
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