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Improved Synthesis of the Triazacryptand (TAC) and its Application in the Construction of a Fluorescent TAC‐BODIPY Conjugate for K + Sensing in Live Cells
Author(s) -
Sui Binglin,
Yue Xiling,
Tichy Michael G.,
Liu Taihong,
Belfield Kevin D.
Publication year - 2015
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.201403600
Subject(s) - bodipy , chemistry , conjugate , fluorescence , cryptand , selectivity , yield (engineering) , combinatorial chemistry , nanotechnology , organic chemistry , catalysis , ion , materials science , mathematical analysis , physics , mathematics , metallurgy , quantum mechanics
In this report, a vastly improved method for the synthesis of [2.2.3]‐triazacryptand (TAC), an excellent K + ‐selective cryptand, is disclosed, which provides a shorter synthetic route with > fivefold higher overall yield. On the basis of the improved synthesis, a TAC‐BODIPY conjugate was developed for K + sensing. TAC‐BODIPY is a fluorescence turn‐on K + sensor exhibiting high selectivity toward K + over other biologically relevant metal cations. Cell imaging studies are presented and demonstrate that TAC‐BODIPY is suitable for dynamic K + sensing in live cells.