Responsive Supramolecular Sensors Based on Pillar[5]arene-BTD Complexes for Aqueous Sensing: From Static Quenching to Anion and DNA Recognition.

ABSTRACT: We report the design and investigation of supramolecular guest-host systems based on cationic pillar[5]-arene macrocycles and fluorescent 2,1,3-benzothiadiazole (BTD) derivatives. The BTD guests, obtained through Sonogashira cross-coupling, display intense visible emission, large Stokes shifts, and strong solvatochromism, while the pillar[5]-arene hosts enable selective recognition in aqueous media. Spectrofluorimetric titrations and NMR experiments revealed the formation of 1:1 inclusion complexes between dianionic BTD derivatives and cationic pillar[5]-arenes, with binding constants on the order of 10⁵ M^-1. Static fluorescence quenching was observed upon complexation, in agreement with molecular docking simulations (ΔG ≈ -8.5 kcal mol^-1) that highl

SUBMITTER: Silva da Conceicao DK 

PROVIDER: S-EPMC12809561 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature