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A theoretical investigation of intermolecular interaction of a phthalimide based “on–off” sensor with different halide ions: tuning its efficiency and electro-optical properties

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Abstract

The interaction between chemosensor, N-(2-methyl-1,3-dioxo-indan-5-yl)-benzamide (1) and different halide ions (F−, Cl− and Br−) has been investigated using density functional theory (DFT). A clear insight of the sensor anion binding process has been presented. Our calculations revealed that the observed colorimetric and fluorescent signals are induced due to the ground state deprotonation of the sensor molecule caused by F− which has two times higher binding affinity than other halide ions (Cl− and Br−). Derivatives of system 1 have been made to find a better sensor with higher binding affinity and longer wavelength of absorption. All the derivatives are better sensors than the parent 1 except 4-methyl-N-(2-methyl-1,3-dioxo-indan-5-yl)-benzamide (2). Among these derivatives, trimethyl-[4-(2-methyl-1,3-dioxo-indan-5-ylcarbamoyl)-phenyl]-ammonium (8) and (5-benzoylamino-1,3-dioxo-indan-2-yl)-trimethyl-ammonium (9) showed a change to higher binding energies of about 58 Kcal/mol and longer absorption wavelengths of 53 nm after deprotonation process than the parent system 1 which is highly demanded in selective chemical sensing. Systems 8, 9 and their deprotonated zwitterionic forms (8z and 9z) have also been studied for their nonlinear optical responses. Systems 8, 9 showed significantly good first hyperpolarizability (β) of 84 × 10−30 and 40 × 10−30 esu, respectively. These β values increase in zwitterionic states up to 216 × 10−30 and 109 × 10−30 esu, respectively after deprotonation with F−, representing a new signal of deprotonation.

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Acknowledgments

The authors acknowledge the financial support from the National Natural Science Foundation of China (Project Nos. 20573016), Training Fund of NENU’S Scientific Innovation Project (NENU-STC07017) and Science Foundation for Young Teachers of Northeast Normal University (20070304), and are supported by Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT). S.Muhammad also acknowledges Ministry of Education, Pakistan and China scholarship council (CSC) for the award of scholarship in Ph.D. program.

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  1. Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University, 130024, Changchun, People’s Republic of China

    Shabbir Muhammad, Chunguang Liu, Liang Zhao, Shuixing Wu & Zhongmin Su

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  1. Shabbir Muhammad
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Correspondence to Zhongmin Su.

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Muhammad, S., Liu, C., Zhao, L. et al. A theoretical investigation of intermolecular interaction of a phthalimide based “on–off” sensor with different halide ions: tuning its efficiency and electro-optical properties. Theor Chem Account 122, 77–86 (2009). https://doi.org/10.1007/s00214-008-0486-8

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