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Solvent Effects on the Photophysical Properties of a Donor–acceptor Based Schiff Base

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Abstract

In this work, a donor–acceptor substituted aromatic system ((E)-N-((E)-3-(4 (dimethylamino)phenyl) allylidene)-4-(trifluoromethyl) benzenamine (DPATB) has been synthesized and its detailed photophysics of intramolecular charge transfer process have been explored on the basis of steady state absorption, fluorescence and time resolved spectroscopy in combination with density functional theory calculations. Large solvent dependency fluorescence spectral shift and the calculated large excited state dipole moment clearly indicate an efficient charge transfer occurring from the donor group to the acceptor moiety in the excited state. Effect on addition of acid and pH on steady state spectral properties further reveals excited state charge transfer character. Quantum chemical calculations were performed in order to study the conformation and polarity of DPATB at their ground as well as excited electronic states. The HOMO and LUMO molecular orbital pictures are obtained at DFT level using B3LYP functional and 6–311 + g(d,p) basis set which clearly support excited state intramolecular charge transfer process. The molecular electrostatic potential maps for the optimized ground state, donor twisted and acceptor twisted geometry shed insight on the electrostatic potential and charge distribution in a system which gives information about the reacting site of the probe and nature of the reaction.

Graphical abstract

In this work, detailed photophysics of excited state intramolecular charge transfer process in donor–acceptor system (DPATB) was evaluated using steady state and time-resolved fluorescence spectroscopy in combination with density functional theory calculations. Large solvent dependency fluorescence spectral shift and the calculated large excited state dipole moment clearly indicate an efficient charge transfer occurring in DPATB. Molecular orbital pictures as obtained from DFT based computational analysis reveals a significant change in the distribution of electron density upon transition from HOMO to LUMO which confirms an ICT process occurring from the donor group to the acceptor moiety in the excited state.

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Acknowledgements

Financial supports from SERB (project file No. EEQ/2019/000210), Government of India was acknowledged by Dr. T. Sanjoy Singh. The authors are indebted to Prof. Samita Basu and her research scholars for their help in fluorescence lifetime measurements. The authors are also highly acknowledged to CSIR-NEIST, Jorhat, CIF, IIT Guwahati for providing NMR and Mass spectra.

Funding

SERB, Government of India (Project file No. EEQ/2019/000210).

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Authors and Affiliations

  1. Department of Chemistry, Assam University, Silchar, Assam, India

    Surjatapa Nath & T. Sanjoy Singh

  2. Department of Physics, Assam University, Silchar, India

    Barnali Bhattacharya & Utpal Sarkar

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  1. Surjatapa Nath
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  2. Barnali Bhattacharya
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  3. Utpal Sarkar
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  4. T. Sanjoy Singh
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Contributions

Surjatapa Nath: Investigation, Validation, Data curation, Writing—original draft. Barnali Bhattacharya: Investigation, Validation, Data curation. Utpal Sarkar: Formal analysis, Data curation. Takhellambam Sanjoy Singh: Methodology, Conceptualization, Writing—review and editing, Resources, Supervision. All authors read and approved the final manuscript.

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Correspondence to T. Sanjoy Singh.

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Highlights

➢ Detailed photophysics of a synthesized donor–acceptor system has been investigated

➢ Newly synthesized compound is found to exhibit intramolecular charge transfer

➢ Protonation at the donor moiety restricts the charge transfer phenomena

➢ HOMO–LUMO picture depicts the intramolecular transfer of electron density

➢ MEP maps clearly visualized the redistribution of electronic charge separation

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Nath, S., Bhattacharya, B., Sarkar, U. et al. Solvent Effects on the Photophysical Properties of a Donor–acceptor Based Schiff Base. J Fluoresc 32, 1321–1336 (2022). https://doi.org/10.1007/s10895-022-02905-6

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