Insights into biomimetic system–ligand interaction of substituted isophthalic acid: A functionality induced photophysical study

Abstract

The present article attempts to interpret the modulation of photophysical properties of isophthalic acid (IPA) through its amino [5‐amino isophthalic acid (5‐amino IPA)] and azido [5‐azido isophthalic acid (5‐azido IPA)] substituted derivatives which are chemically potent organic ligands. The ground state structure–reactivity correlation of 5‐amino IPA and 5‐azido IPA has been deciphered through computational studies. The computed energetics show significant interaction feasibility of the substituted ligand systems with the biomimetic systems which is further validated experimentally. The binding interaction of the probes with oppositely polarized functionalization is studied to be significant with cetyltrimethylammonium bromide (CTAB) and bovine serum albumin (BSA) with the amino functionalized derivative having a comparatively stronger binding constant value. The steady‐state absorption and fluorescence study establish significant modification of polarity of the heteronuclear probes. The micro polarity study in water–dioxane mixtures enables determination of polarity of 5‐amino IPA in CTAB and BSA unlike 5‐azido IPA. Presence of an overlapping region between the emission spectrum of BSA and the absorption spectrum of the probes as probable donor–acceptor pair are also scrutinized via the steady‐state fluorescence studies. The photophysical behavior of 5‐amino IPA is observed to be somewhat dissimilar to that of 5‐azido IPA.