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. 2025 Apr 29;31(5):148.
doi: 10.1007/s00894-025-06366-z.

Theoretical investigation of naphthodithiophene diimide derivatives as fluorescent sensors for 2,4,6-trinitrophenol detection

Leixing Luo  1 , Mingxuan Dang  1 , Xiaoming Song  1 , Qingxia Zhao  1 , Shuo Yang  2 , Xiufang Hou  3 , Shuai Liu  1 , Yixia Ren  4
Affiliations

Theoretical investigation of naphthodithiophene diimide derivatives as fluorescent sensors for 2,4,6-trinitrophenol detection

Leixing Luo et al. J Mol Model. .

Abstract

Context: This study explored the geometry, aromaticity, electrostatic potential, and fluorescence sensing capability of N,N'-dimethyl naphthodithiophene diimide (C1-NDTI-S) and its derivatives (C1-NDFI-O and C1-NDPI-N), where thiophene rings were substituted with furan and pyrrole, respectively. Theoretical calculations revealed that C1-NDTI-S had the most negative adsorption energy for 2,4,6-trinitrophenol (TNP), and its electronic absorption spectrum and fluorescence spectrum decreased considerably upon TNP adsorption. Through FMO, hole-electron, independent gradient model, and energy decomposition analysis, it was revealed that the essence of fluorescence quenching is the intermolecular weak π-π interaction driving photo-induced electron transfer. Furthermore, C1-NDFI-O and C1-NDPI-N generated by modifying the structure of C1-NDTI-S have the potential to serve as more efficient fluorescent sensors for TNP detection. The fluorescence recovery times confirmed the suitability of the three compounds as fluorescence probes.

Methods: In this study, the Gaussian 09 software package at B3LYP-D3(BJ)/6-311 + + G** level was applied to optimize the structure, energy, and fluorescence recovery time. Multiwfn combined with VMD software package was used to analyze the aromaticity of compounds using LOL-π and HOMA, with a focus on the differences in aromaticity after thiophene was substituted with different rings. Using AMBER force field for energy decomposition analysis based on force field (EDA-FF), the weak intermolecular interaction components are decomposed. The independent gradient model analysis based on Hirshfeld partition analysis clearly demonstrates the π-π interactions between molecules, with the δginter parameter set to 0.005 a.u. Electron absorption spectroscopy, charge-transfer spectra spectroscopy, molecular interactions, and hole electron interactions were all completed with the help of Multifwn software.

Keywords: 2,4,6-trinitrophenol; Density functional theory; Fluorescence quenching; Naphthodithiophene diimide; Photo-induced electron transfer; Recovery time.

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Conflict of interest statement

Declarations. Competing interests: The authors declare no competing interests.

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