Tunable solvatochromic response of newly synthesized antioxidative naphthalimide derivatives: intramolecular charge transfer associated with hydrogen bonding effect.
ABSTRACT The solvatochromic behavior of two newly synthesized naphthalimide derivatives (I and II) which have potential antioxidative activities in anticarcinogenic drug development treatment, has been monitored in protic and aprotic solvents of different polarity applying steady-state and time-resolved fluorescence techniques. The compounds exhibit unique photophysical response in different solvent environments. The spectral trends do not appear to originate only from changes in the solvent polarity but also indicate that hydrogen bonding interactions and intramolecular charge transfer (ICT) influence the energy of electronic excitation of the compounds. Incorporation of an amino group at C(4) position of the naphthalimide ring in II makes it behave differently from I in terms of spectral characterization and fluorescence efficacy of the systems. The nonradiative relaxation process of the compounds is governed by medium polarity. The ground state geometry, lowest energy transition, and the UV-vis absorption energy of the compounds were studied using density functional theory (DFT) and time-dependent density functional theory (TDDFT) at the B3LYP/6-31G* level, which showed that the calculated outcomes were in good agreement with experimental data.
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ABSTRACT: The spectral characteristics of N,N-dimethyl-4-(4-methyl-4H-imidazo[4,5-b]pyridin-2-yl)benzenamine (PyN-Me), 1-methyl-2-(4'-(N,N-dimetylaminophenyl)imidazo[4,5-b] pyridine (ImNH-Me) and 2-phenylimidazo[4,5-b]pyridine (PIP) are investigated to understand the mechanism of protic solvent induced dual fluorescence of 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (DMAPIP-b). No dual emission is observed from PyN-Me where pyridyl nitrogen is blocked from hydrogen bonding with protic solvents confirms the importance of hydrogen bonding of protic solvents with the pyridyl nitrogen in dual emission of DMAPIP-b. Like DMAPIP-b, ImNH-Me also exhibits weak emission and has shorter fluorescence lifetime in methanol. However single emission is observed from ImNH-Me in all solvents including protic solvents. This suggests that the imidazole hydrogen also plays a role in the dual emission process. The longer wavelength emission of DMAPIP-b in water increases with increase in pH of the solution owing to deprotonation of imidazole >NH group. Based on these results the mechanism for the dual emission of DMAPIP-b is proposed.The Journal of Physical Chemistry B 07/2013; · 3.61 Impact Factor
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ABSTRACT: A series of imidazole derivatives connected with pyridine moiety through phenyl groups were synthesized by using Suzuki coupling followed by multicomponent cyclization reaction. Results obtained from spectroscopic ((1)H NMR, (13)C NMR, Mass) and single crystal X-ray diffraction analysis of synthesized compound was in very good agreement with its chemical structure. UV-Vis and fluorescence studies in various solvents with different polarity demonstrated that these compounds were sensitive to the polarity of the microenvironment. In addition, multi linear regression analysis based on Kamlet-Taft and Catalán new four parameter solvent scale results in solvatochromism and was mainly influenced by solvent polarisability and dipolarity of the environment. The electrochemical stability of the compounds was also studied by cyclic voltammetry. An excellent fluorescent nature with high quantum efficiency of the compounds was successfully utilized to probe the bacteria by using fluorescence microscopy. In addition, the antibacterial and antifungal activity of these compounds were also studied in vitro by the disk diffusion assay against one Gram-positive, three Gram-negative bacteria and Candida albicans. MPBI showed relatively good inhibitory action against Gram-negative bacteria and TPBI against Gram-positive bacteria and 3PBI against C. albicans.Journal of photochemistry and photobiology. B, Biology 09/2013; 127C:212-222. · 1.87 Impact Factor