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Photoinduced processes in macrocyclic isoalloxazine–anthracene systems

Paper ID Volume ID Publish Year Pages File Format Full-Text
26380 43949 2016 9 PDF Available
Title
Photoinduced processes in macrocyclic isoalloxazine–anthracene systems
Abstract

Two new macrocyclic structures containing 8-hidroxyisoalloxazine and 1,5-dihydroxyanthracene moieties linked by aliphatic chains of different lengths (n = 4 and 6) were designed and synthesized in order to study photoinduced electron transfer (PET) processes from the anthracene unit towards the isoalloxazine singlet excited state induced by structural changes due to different intrachromophoric distances and orientations. The compounds have been fully characterized by NMR spectroscopy and the X-ray solid state structures of both macrocycles have been elucidated. Photophysical measurements, including continuous wavelength photoinduced absorption (cw-PIA), at room temperature and 77 K have been carried out in order to investigate the influence of the close contacts between the aromatic groups (π–π stacking) on the photophysical properties of the macrocycles.

Graphical abstractTwo new macrocycles containing isoalloxazine and anthracene moieties linked by aliphatic chains of different lengths have been synthesized. The length of the aliphatic chain linkers brings about structural changes that provide different intrachromophoric orientations leading to the tuning of the rate of photoinduced electron transfer from the anthracene unit towards the isoalloxazine singlet excited state.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
FAD, flavin adenine dinucleotide; FMN, flavin monononucleotide; BLUF, blue light photoreceptors; CRY, cryptochrome; NMR, nuclear magnetic resonance; PLQY, photoluminescence quantum yield; cw-PIA, continuous wavelength photoinduced absorption; PET, photoin
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Photoinduced processes in macrocyclic isoalloxazine–anthracene systems
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 314, 1 January 2016, Pages 189–197
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering