Dye Modified Phenylenediamine Oligomers: Theoretical Studies on Drug Binding for Their Potential Application in Drug Sensors

Ufana Riaz; Syed Marghoob Ashraf

doi:10.1021/acsphyschemau.3c00025

Dye Modified Phenylenediamine Oligomers: Theoretical Studies on Drug Binding for Their Potential Application in Drug Sensors

ACS Phys Chem Au. 2023 Aug 28;3(6):521-531. doi: 10.1021/acsphyschemau.3c00025. eCollection 2023 Nov 22.

Authors

Ufana Riaz^{1

2}, Syed Marghoob Ashraf²

Affiliations

¹ Department of Chemistry and Biochemistry, North Carolina Central University, Durham, North Carolina 27707, United States.
² Materials Research Laboratory, Department of Chemistry, Jamia Millia Islamia, New Delhi 110025, India.

Abstract

The present work reports, for the first time, synthesis of dye incorporated o-phenylenediamine (OBB) with a view to obtain a conjugated oligomer with enhanced functionality. The structure was confirmed by IR studies, while the electronic transitions were confirmed by UV visible studies. The dye modified oligomer showed one order higher fluorescence intensity than the pristine Bismarck Brown (BB) dye. Confocal imaging showed red emission which could be utilized in near infra-red imaging. Density functional theory (DFT) studies were carried out to predict the theoretical properties of the oligomers. The energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital orbital were computed to explore how the HOMO energies of the reactants initiated the electronic interactions between them. The interaction energies were correlated to conjugation/hyper conjugation stabilization energies of the natural bond orbitals (NBO) via the DFT method using the B3LYP functional with the 6-311G(d) basis set on Gaussian 09 software. Drug binding was evaluated through simulation of interaction energy, (ΔE_A-x) with drugs such as captopril, propranolol, thiazide, and fentanyl. The results predicted that the oligomer could be developed into a fentanyl drug sensor.