Spectroscopic and Quantum Mechanical Approach of Solvatochromic Immobilization: Modulation of Electronic Structure and Excited-State Properties of 1,8-Naphthalimide Derivative

Abstract

Photophysical and spectroscopic properties of a fluorescent analogue, 2-(5-selenocyanato-pentyl)-6-chlorobenzo- [de]isoquinoline-1,3-dione (NP) in different solvents has been described in this paper using steady-state, time resolved spectroscopy and density functional theory (DFT) calculation. Stoke's shifted emission band in different solvents clearly demonstrate the highly polar character of the excited state, which is also supported by the enhancement of dipole moment of the molecule upon photoexcitation. Spectroscopic studies and multiple linear regression analysis method reveal that the solvatochromic behavior of the probe depends not only on the polarity of the medium but also on the hydrogen bonding interaction with the solvents. When the solvent effect was taken into account, the computed results show encouraging agreement with known experimental data. This article reveals the excellent correlation between the predicted and experimental spectral data of 1,8-naphthalimide derivative, providing a useful tool in the design of new fluorogenic probes having potential therapeutic activity.

A “weak acid and weak base” type fluorescent probe for sensing pH: mechanism and application in living cells

“…Additionally, NDI derivatives show excellent environmental sensitivity and a strong internal charge transfer (ICT) character. [31][32][33] Therefore, they have great potential for developing uorescent probes. [34][35][36][37] Here, we report a 1,8-naphthalimide derivative, Naphthalimideisoniazid hybrid NDI as a new pH-sensitive probe with a suitable pK a 1 (4.50) and pK a 2 (9.34) for biosystem investigation.…”

Experimental spectra, electronic properties (liquid and gaseous phases) and activity against SARS-CoV-2 main protease of Fluphenazine dihydrochloride: DFT and MD simulations

“…S3) at the B3LYP/6-311++G* level of theory. It is used to calculate FDD's band gap and higher values indicate that tightly bound valence electrons with nucleus [68] . Gas and water get the same wavelength 276.72 nm, band 4.4805 eV, energy 36137.67 cm −1 and oscillatory strength 0.065 with contribution 85% ( table 2 ).…”

Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing

“…Naphthalimide derivatives are of interest due to their promising properties such as strong emission, high quantum efficiency, good photostability, thermal stability, film-forming ability, etc. [ 1 , 2 , 3 , 4 , 5 ]. These versatile characteristics make naphthalimides potential materials for fluorescent sensors and molecular switchers, laser active media, light emitting diodes, dyes for natural synthetic fibers, fluorescent markers in biology, antitumor treatments, DNA targeting binders, and photoinitiators [ 2 , 3 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ].…”

“…The absorption and fluorescence spectra of naphthalimides are sensitive to the polarity of the surrounding environment and some solvent mediated spectral investigations were performed until now [ 4 , 17 , 20 , 33 , 34 ]. The solvatochromic features of the naphthalimide derivatives made them excellent candidates for fluorescent sensors for water detection in solution because the emission is strongly dependent on the solvent polarity and it is quenched even at low water levels [ 35 , 36 , 37 ].…”