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.
[Show abstract][Hide abstract] ABSTRACT: The excited state intramolecular charge transfer process in donor–chromophore–acceptor system 5-(4-dimethylamino-phenyl)-penta-2,4-dienenitrile (DMAPPDN) has been investigated by steady state absorption and emission spectroscopy in combination with Density Functional Theory (DFT) calculations. This flexible donor acceptor molecule DMAPPDN shows dual fluorescence corresponding to emission from locally excited and charge transfer state in polar solvent. Large solvatochromic emission shift, effect of variation of pH and HOMO–LUMO molecular orbital pictures support excited state intramolecular charge transfer process. The experimental findings have been correlated with the calculated structure and potential energy surfaces based on the Twisted Intramolecular Charge Transfer (TICT) model obtained at DFT level using B3LYP functional and 6-31+G(d,p) basis set. The theoretical potential energy surfaces for the excited states have been generated in vacuo and acetonitrile solvent using Time Dependent Density Functional Theory (TDDFT) and Time Dependent Density Functional Theory Polarized Continuum Model (TDDFT-PCM) method, respectively. All the theoretical results show well agreement with the experimental observations.
[Show abstract][Hide abstract] ABSTRACT: Entrapping of a fluorogenic material comprising prospective therapeutic activity in microhetrogeneous environments and modulating important photophysical properties is highly desirable as far as potential applications of such systems are concerned. The present work demonstrates the interesting photobehavior of a newly synthesized antioxidative naphthalimide (isoquinolinedione) derivative (ANAP) in micellar solutions of anionic sodium dodecyl sulphate (SDS), cationic cetyl trimethylammonium bromide (CTAB) and nonionic p-tert-octylphenoxy polyoxyethanol (TX-100) surfactants using steady-state, time-resolved fluorescence and fluorescence anisotropy techniques. The remarkable sensitivity of the fluorescence properties of ANAP to the polarity of the media is attributed to the existence of a fluorescent intramolecular charge transfer (ICT) state. ANAP is found to be an excellent fluorescence sensor for following the micellar aggregation process. Fluorometric studies suggest that the probe resides at the micelle–water interface in all these systems. The present effort endeavors the degree of accessibility of the fluorophore toward the metal ion quencher in the presence of micelles of different surface charge characteristics. The enhancements in the steady-state anisotropy and rotational relaxation time in the micellar media compared to that in pure aqueous solution reflect that the fluorophore resides in a motionally restricted environment introduced by the micelles.
Colloids and Surfaces A Physicochemical and Engineering Aspects 05/2012; 402:117–126. DOI:10.1016/j.colsurfa.2012.03.035 · 2.75 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Water-soluble hydrophobic-dye@nano-hybrids (DPN@NHs) with extraordinarily enhanced fluorescent performance were fabricated by encapsulating the hydrophobic dye molecules into the core of the hybrid nanospheres based on the self-assembly of amphiphilic block copolymers followed by shell cross-linking using 3-mercaptopropyltrimethoxy-silane. The DPN@NHs are 50 nm in size, are monodispersed in aqueous solution and have a quantum yield enhanced by 30 times.
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