Turn-on fluorescence response upon anion binding to dimesitylboryl-functionalized quaterthiophene

Abstract

Addition of CN(-) or F(-) to the B-functionalized quaterthiophene QTB induces a rapid change in the emission color from yellow to blue and blue-green, respectively, accompanied by a strong fluorescence turn-on. Structural analyses and TD-DFT calculations suggest that both the conformation of the conjugated backbone and the nature of the anion have a critical impact.

Recent developments in and perspectives on three-coordinate boron materials: a bright future

“…180,181 Yamaguchi previously reported side-chain BMes 2 -containing systems to be very efficient solid-state fluorescent materials. 182,183 Enhanced anion binding strength by introduction of cationic groups was also reported for the side-chain polymers.…”

Synthesis, Coupling, and Condensation Reactions of 1,2‐Diborylated Benzenes: An Experimental and Quantum‐Chemical Study

“…The scope of arylboranes can be further expanded when two (or more) boryl substituents are introduced into the same arene system: With respect to synthesis, such compounds offer the possibility of performing double cross‐coupling reactions with aromatic (di)halides as a synthetic route to functionalized PAHs (e.g., oligophenyls, phenanthrenes, and dibenzo[ g , p ]chrysenes) 26–29. In the case of boron‐based (co)catalysts, cooperative binding can lead to improved catalytic performance30–36 and, in the case of chemosensors, signal‐amplification has been reported 37–41…”

“…[26][27][28][29] In the case of boron-based (co)catalysts, cooperative binding can lead to improved catalytic performance [30][31][32][33][34][35][36] and, in the case of chemosensors, signalamplification has been reported. [37][38][39][40][41] Therefore, efficient synthetic routes to oligoborylated arenes are in great demand, especially to afford arenes that contain boryl groups at adjacent positions on the ring. 1,2-Diborylbenzenes are prototypical examples of vicinal diborylated arenes and various different strategies for their preparation have been developed; however, many of these syntheses suffer from distinct disadvantages, such as: 1) The reaction of 1,2-C 6 H 4 A C H T U N G T R E N N U N G (EMe 3 ) 2 (E = Si, Sn) with BCl 3 provides a route to 1,2-bis(dichloroboryl)benzene (1,2-C 6 H 4 -A C H T U N G T R E N N U N G (BCl 2 ) 2 ); [42] however, BCl 3 is a hazardous, highly corrosive chemical and 9,10-dichloro-9,10-dihydro-9,10-diboraanthracene (ClBA C H T U N G T R E N N U N G (m-C 6 H 4 ) 2 BCl), as well as partially methylated boranes, are often formed as major byproducts of the Si/B-ex-Abstract: 1,2-Bis(pinacolboryl)benzene (1,2-C 6 H 4 A C H T U N G T R E N N U N G (Bpin) 2 , 2) was synthesized in preparatively useful yields from 1,2-C 6 H 4 Br 2 , iPrO À Bpin, and Mg turnings in the presence of 1,2-C 2 H 4 Br 2 as an entrainer.…”

Ratiometric fluorescence detection of fluoride ion by indole-based receptor

“…Selective recognition and sensing of anionic species via artificial receptors have recently emerged as an important multidisciplinary research field across biology, chemistry, and environment science [1][2][3][4][5][6], considering the vital roles of anions in our daily life. Among various anions, fluoride ion (F À ), one of the most important nucleophilic anions, is of particular interest owing to its extensive application in dental health and clinical treatment for osteoporosis [7][8][9][10][11].…”