Structure-Property Correlations in Disubstituted 1,2,3-Triazoles - DFT Insights and Photophysical Analysis

Sep 29, 2026

Disubstituted 1,2,3-triazoles combine structural rigidity with tunable electronic characteristics, enabling adaptable use in photophysical and supramolecular chemistry. The study integrates experimental and computational analysis of 1,4- and 1,5-disubstituted derivatives, including hydroxyaromatic and nonhydroxyaromatic frameworks. Solvatochromic effects are examined in medium-polarity solvents and photophysical responses are tracked across pH via protonation/deprotonation pathways. Spectroscopy is supported by B3LYP/6-311G(d,p) DFT and TD-DFT, complemented with NBO analysis for key hydroxy and nonhydroxy triazoles.

LanguageEnglish

CategoryResearch & Report

FormatPDF

Pages18

Reading Time45 min

AccessFree to download

Abstract

Introduction

Applications of 1,2,3-triazoles in photonics and sensing

This article is licensed under CC-BY 4.0 [http://pubs.acs.org/journal/acsodf](http://pubs.acs.org/journal/acsodf) Article Structure−Property Correlations in Disubstituted 1,2,3-Triazoles: DFT Insights and Photophysical Analysis Published as part of ACS Omega special issue “Undergraduate Research as the Stimulusfor Scientific Progress in the USA”. Dharatiben Lakhani, Sheeba Sadiq, Harini Subbaiahgari, Violet Swanson, Jacob Munyon, Sher B. Poudel, Karelle S. Aiken, Shainaz M. Landge, Debosreeta Bose, * and Debanjana Ghosh * Cite This: ACS Omega 2025, 10, 58925−58942 Read Online | | | | | | | | --- | --- | --- | --- | --- | --- | | ACCESS | Metrics & More | | Article Recommendations | | *sı Supporting Information | ABSTRACT: The inherent structural rigidity and modifiable electronic features of disubstituted 1,2,3-triazoles are driving their recognition as adaptable frameworks in photophysical and supramolecular chemistry. The combination of structural integrity and tunable electronic characteristics makes 1,2,3-triazoles highly functional for a wide range of applications, from fluorescence-based sensors and drug design to organic electronics. Owing to the versatile applications of triazoles in multiple domains, this study integrates experimental and computational analysis of a series of 1,4-and 1,5-disubstituted 1,2,3-triazole derivatives. To elucidate the electronic architecture, photophysical characteristics, and structure−property correlations, 1,2,3-triazoles with and without ahydroxyaromatic framework have been investigated. Emphasis has been given to the molecules’ solvatochromic behavior in mediumpolarity solvents. The photophysical behavior of the studied 1,2,3-triazole molecules is also modulated by pH, reflecting changes via a protonation/deprotonation pathway specific to the individual molecules. Systematic spectroscopic investigations revealed differential absorption and emission responses across acidic to basic environments, highlighting the sensitivity of triazole chromophores to proton-coupled electronic interactions. Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) calculations at the B3LYP/6-311G(d,p) level were employed to investigate the frontier molecular orbitals (FMOs), electron density distributions, and polarity of the studied molecules, with outcomes corroborated by UV−vis and fluorescence spectroscopic measurements. Additionally, Natural Bond Orbital (NBO) analysis is performed for 2-(4-phenyl-1-H-1,2,3-triazol-1-yl) phenol (PTP) and 5-anilino-4-phenyl-1H-1,2,3-triazole (APT), representing hydroxyaromatic and nonhydroxyaromatic triazoles, respectively. This analysis primarily focuses on establishing the photophysical characteristics of the molecules as being of a charge-transfer nature and their inherent electron density distribution. A comparative analysis of experimental and computational data revealed a consistent and complementary trend, reinforcing the reliability of the interpretations drawn from both approaches. 1. INTRODUCTION The five-membered heterocycles with aromatic character present a versatile group of compounds possessing rich chemical functionality. In particular, 1,2,3-triazoles have emerged as valuable components in the design of organic dyes, fluorescent metal ion sensors, OLED materials, corrosion inhibitors, and catalysts.1,2 Among their structural isomers, the 1,4- and 1,5-disubstituted 1,2,3-triazoles have gained wide- | Received: July 31, 2025
Revised: November 10, 2025
Accepted: November 13, 2025
Published: November 24, 2025 | | | --- | --- | © 2025 The Authors. Published by American Chemical Society 58925 [https://doi.org/10.1021/acsomega.5c07623](https://doi.org/10.1021/acsomega.5c07623) ACS Omega 2025, 10, 58925−58942 Scheme 1. Structures of (a) PTP, (b) NpTP,(c) PhTP,(d) ADT, and (e) APT spread attention due to their ease of synthesis, regioselectivity, and broad applicability across disciplines. The c

FAQs

What aspects of disubstituted 1,2,3-triazoles are central to the study?

The work focuses on structural rigidity and modifiable electronic features, linking them to photophysical behavior and structure–property correlations.

How are solvatochromic and pH-dependent behaviors investigated?

Solvatochromic behavior is evaluated in medium-polarity solvents, and pH effects are examined by tracking protonation/deprotonation changes that vary by individual molecules.

Which computational methods support the experimental photophysical measurements?

B3LYP/6-311G(d,p) DFT and TD-DFT calculations are used to analyze frontier molecular orbitals, electron density, and polarity, while UV–vis and fluorescence spectroscopy corroborate the results. Natural Bond Orbital analysis is applied to specific triazole derivatives.

Sep 29, 2026

Upload by วิน