Acidochromic Behavior of Dibenzylidene Cyclohexanone-Based Bischalcone: Experimental and Theoretical Study

Area of Science:

• Organic Chemistry
• Computational Chemistry
• Materials Science

Background:

• Chalcones and their derivatives are known for diverse biological and optical properties.
• Bis نسخةchalcone structures offer unique electronic and structural characteristics.
• Understanding structure-property relationships is crucial for designing new functional materials.

Purpose of the Study:

• To synthesize and characterize novel 2,6-dibenzylidene cyclohexanone-based bischalcone derivatives.
• To investigate the acidochromic and solvatochromic properties of these compounds.
• To determine the optimized molecular geometries and electronic properties using computational methods.

Main Methods:

• Synthesis of bischalcone derivatives.
• Characterization using UV-Vis, FTIR, 1H NMR, and elemental analysis.
• Density Functional Theory (DFT) calculations for geometry optimization and energy analysis (B3LYP/6-311G+(d,p) and APFD/6-311+G(d,p)).

Main Results:

• Successful synthesis and characterization of novel bischalcone derivatives.
• Compound 1e exhibited significant acidochromic behavior due to preferential protonation of the N,N-dimethylamino group.
• Computational studies supported the experimental findings, showing a favorable protonation energy of 211 kcal/mol for compound 1e.
• Solvatochromic behavior was also observed.
• The APFD/6-311+G(d,p) basis set provided the lowest energy values for the optimized geometries.

Conclusions:

• The synthesized bischalcone derivatives possess interesting optical properties, including acidochromism and solvatochromism.
• DFT calculations are valuable tools for predicting and understanding the electronic and structural properties of these compounds.
• Compound 1e shows potential for applications where pH-dependent color changes are desired.