학술논문
Molecular Engineering To Enhance Reactivity and Selectivity in an Ultrafast Photoclick Reaction.
Document Type
Article
Author
Source
Subject
*FLUORESCENCE yield
*ORTHOGONAL systems
*PHOTOINDUCED electron transfer
*ALKENES
*ENGINEERING
*NANOPARTICLES
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Language
ISSN
0044-8249
Abstract
Light‐induced 9,10‐phenanthrenequinone‐electron‐rich alkene (PQ‐ERA) photocycloadditions are an attractive new type of photoclick reaction, featuring fast conversions and high biocompatibility. However, the tunability of the reaction was hardly investigated up to now. To this end, we explored the influence of substituents on both reaction partners and the reaction rate between the PQs and ERAs. We identified new handles for functionalization and discovered that using enamines as ERAs leads to drastically enhanced rates (>5400 times faster), high photoreaction quantum yields (ΦP, up to 65 %), and multicolor emission output as well as a high fluorescence quantum yield of the adducts (ΦF, up to 97 %). Further investigation of the photophysical and photochemical properties provided insights to design orthogonal reaction systems both in solution and on nanoparticle surfaces for ultrafast chemoselective functionalization by photoclick reactions. [ABSTRACT FROM AUTHOR]