Structural and solvent effects on the spectroscopic properties of 1, 8‐naphthalimide derivatives: A density functional study

Abstract

The molecular structures of 1, 8-naphthalimide derivatives were investigated at density functional theory level within framework of PBE1PBE/6-31G*. The vertical ionization potential and their delocalization energy of the X-ray solid structure and gas-phase optimized structure were explored. The configuration difference between them was attributed to the p-p interaction of the solid effect, which has negligible effect on their absorption spectra. Solid effect also weakens the intramolecular interaction. Their absorption and luminescent spectra in gas and solvent phase were calculated by time-dependent density functional theory (TDDFT) and conductor polarizable continuum models (CPCM)-TDDFT approaches. Obvious red shifts from the solvent effect were found. Substituents on the imides will not improve their spectra properties a lot, whereas substituents on the naphthalene of naphthalimide would modify their properties to emit different spectra. Systematical deviation of vertical excitation energy from absorption and emission spectra, obtained by CPCM-PBEPBE/6-31G* and CIS-CPCM-PBEPBE/6-31G* models, were about 0.05 eV and 0.02 eV compared with the experimental values.

Experimental and theoretical study on the absorption and fluorescence properties of substituted aryl hydrazones of 1,8-naphthalimide

“…1,8-Naphthalimides have been widely investigated because of their photophysical properties. [1][2][3][4][5][6][7][8] Naphthalimides are one of the most important building blocks for synthesis of efficient fluorescent materials showing large quantum yields and sizable Stokes shifts. Gan and coworkers synthesized some aryl hydrazones of 4-hydrazino-N-butyl-1,8-naphthalimide and studied their electronic and fluorescence spectra for application as materials for light emitting diodes (OLEDs).…”

An efficient, Schiff-base derivative for selective fluorescence sensing of Zn2+ions: quantum chemical calculation appended by real sample application and cell imaging study

“…There are a variety of wave function-based methods such as CIS, CASPT2, SAC-CI, and MP2 to calculate the excited state geometry and optoelectronic properties. 44,45 So to obtain better results, we optimized the ground-and excited-state geometry of PyHP and its complex [PyHP-Zn 2+ ] by DFT/6-31G(d,p) and CIS/6-31G(d,p) methods respectively. We then calculated the absorption and emission spectra using the TD-DFT method 44,46,47 with the B3LYP exchange-correlation functional.…”

Synthesis, Spectroscopic, and Analyte-Responsive Behavior of a Polymerizable Naphthalimide-Based Carboxylate Probe and Molecularly Imprinted Polymers Prepared Thereof

“…In our present work, we chose the 4-amino-substituted naphthalimide (NI) chromophore as the scaffold because such dyes usually emit strong fluorescence in the analytically advantageous region >500 nm and can be excited in the near visible at ca. 420–450 nm, , a range for which low-cost excitation sources are readily available. In addition, the NI unit is a popular building block in fluorescent probes for various analytes, , can be integrated into polymers, , and has also been successfully employed in anion-responsive probes. , On the basis that many of the key targets as templates/analytes in our MIP research carry at least one carboxylic acid group, , the latter features are very interesting and motivated us to pursue the synthesis of the polymerizable NI-based anion probe 1 (Chart ).…”

“…12−14 In our present work, we chose the 4-amino-substituted naphthalimide (NI) chromophore as the scaffold because such dyes usually emit strong fluorescence in the analytically advantageous region >500 nm and can be excited in the near visible at ca. 420−450 nm, 15,16 a range for which low-cost excitation sources are readily available. In addition, the NI unit is a popular building block in fluorescent probes for various analytes, 17,18 can be integrated into polymers, 19,20 and has also been successfully employed in anion-responsive probes.…”