Synthesis and conformation of a novel fluorescein–Zn-porphyrin dyad and intramolecular energy transfer. (7th March 2016)

• Record Type: Journal Article
• Authors: Rezazgui, Olivier; Trouillas, Patrick; Qiu, Shi-hong; Siegler, Benjamin; Gierschner, Johannes; Leroy-Lhez, Stephanie
• Is Part Of: New journal of chemistry. Volume 40:Number 4(2016:Apr.)
• Page Start: 3843
• Page End: 3856
• Publication Date: 2016-03-07
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c5nj02901e
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Modulations of the optical properties of a new porphyrin–fluorescein dyad were elucidated using experimental and theoretical techniques, with conformational rearrangements being studied. Abstract : This study describes the synthesis and characterization of a new zinc porphyrin–fluorescein dyad, the two chromophoric units being covalently linked by a 1, 2, 3-triazole bridge. The latter was formed by Cu-catalyzed Huisgen 1, 3-dipolar cycloaddition. The conformational analysis of this dyad (1 ) was performed by NOESY experiments, suggesting interactions between moieties; density functional theory (DFT) calculations confirmed clear evidence of a folded conformer, which is stabilized by electrostatic and CH–π interactions. Photophysical measurements demonstrated solvent-dependent energy transfer, with an efficiency of about 40%.