New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion

Abstract

Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. CuI catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption–emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated.

Carboxonium derivatives based on closo-dodecaborate anions [1,2-B12H10O2CR]−: synthesis and molecular orbital analysis

“…[22][23][24][25][26][27] Based on the ring opening process, it is possible to create complex organic-inorganic systems in which a boron cluster is attached through a chain of four or five CH 2 groups to organic platforms such as porphyrins, phthalocyanines, calixarenes, coumarins and sterols. [28][29][30] Carboxonium derivatives of boron clusters have received less attention than oxonium derivatives, but derivatives of cobalt bis(dicarbollide) and closo-decaborate anions have been described. 31,32 The authors' research group has focused mainly on the closo-decaborate anion.…”

“…22–27 Based on the ring opening process, it is possible to create complex organic–inorganic systems in which a boron cluster is attached through a chain of four or five CH 2 groups to organic platforms such as porphyrins, phthalocyanines, calixarenes, coumarins and sterols. 28–30…”

Theoretical Insight on the Formation Mechanism of a Trisubstituted Derivative of Closo-Decaborate Anion [B10H7O2CCH3(NCCH3)]0

“…[1][2][3][4][5]. The main approach for the formation of such platforms is the process of the substitution of a hydrogen atom to create different exo-polyhedral substituents [6][7][8][9][10]. Thus, investigation of the substitution process in closo-borate anions is one of the central cornerstones of modern chemistry in relation to boron clusters [11][12][13][14].…”