Premium
Function‐Oriented Synthesis of a Didesmethyl Triazacryptand Analogue for Fluorescent Potassium Ion Sensing
Author(s) -
Carpenter Richard D.,
Verkman Alan S.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001450
Subject(s) - chemistry , fluorescence , chromophore , selectivity , yield (engineering) , combinatorial chemistry , chemical synthesis , photochemistry , organic chemistry , in vitro , biochemistry , catalysis , physics , materials science , quantum mechanics , metallurgy
Abstract Triazacryptand (TAC)‐based fluorescent K + sensors have broad biomedical utility, yet their advancement has been hindered because of their challenging synthesis. Herein, an efficient synthesis is reported that delivers a didesmethyl triazacryptand (ddTAC) K + sensor in twofold fewer steps and ninefold higher overall yield than the original TAC synthesis. Our synthesis utilizes a C–O dianionic oxidative macrocyclization and reports new examples of aminoarylations and a microwave route to xanthythilium chromophores. The K + sensitivity and selectivity of the ddTAC‐based sensor are comparable to the TAC‐based sensor.