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Carbazole-Based Porphyrins: Synthesis, Structure–Photophysical Property Correlations, and Mercury Ion Sensing

Arumugam Kalaiselvan, Isukapalli Sai Vamsi Krishna, Anjana Prasad Nambiar, Aathira Edwin, Sivaranjana Reddy Vennapusa, Sabapathi Gokulnath

2020Organic Letters26 citationsDOI

Abstract

The synthesis of a new class of carbazole based macrocycles via [3 + 1] acid-catalyzed condensation is reported. Spectroscopic investigations and computational studies imply that these macrocycles have a large influence on the electronic structure in comparison to previously reported carbazole based macrocycles. Macrocycle 8 bearing a furan ring reversibly binds aqueous Hg2+ with high affinity over other Mn+ ions. The limit of detection (LOD) is ca. 100 nM. Hg2+ binding was confirmed via X-ray diffraction analysis.

Topics & Concepts

CarbazoleChemistryFuranIonMercury (programming language)Aqueous solutionPyrroleCombinatorial chemistryPhotochemistryOrganic chemistryProgramming languageComputer sciencePorphyrin and Phthalocyanine ChemistryMolecular Sensors and Ion DetectionLuminescence and Fluorescent Materials