Synthesis and structural characterisation of the first bis(bora)calixarene: a selective, bidentate, fluorescent fluoride sensor

Abstract

A bis(bora)calixarene 3, the first lower-rim boron derivatised calixarene to be structurally characterised, is synthesised by the reaction of PhBCl2 with 4-tert-butylcalix[4]arene, and is demonstrated to be a sensitive and selective fluorescent fluoride sensor.

Preparation of fluoride anion responsive poly(N-vinylcarbazole)-borane complexes

“…In these systems, borate formation of organoboron unit with fluoride anion results in interruption of p-conjugation, which leads to blue-shift of absorption and quenching of fluorescence emission. Bidentate type borylated naphthalene derivatives [26][27][28][29][30] were also reported, which showed improved fluoride binding ability compared with monodentate type arylboranes. Recently, cationic triarylboranes that chelate fluoride anion in aqueous environment were also reported by Gabbaï et al [31,32].…”

“…One of approaches to detect fluoride anion has been designing receptor molecule that forms hydrogen bond with fluoride anion [9][10][11][12]. As another major approach, design of arylborane type anion receptor has been widely examined [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36]. In late 1990s, organoboron p-conjugated systems highly extended through the vacant p-orbital were developed by several groups independently [18][19][20][21][22][23].…”

A trivalent organoboron compound as one and two-photon fluorescent chemosensor for fluoride anion

“…Recently, several research groups have reported that trivalent boron compounds can be used as effective colorimetric, fluorescent, or ratiometric sensors for the detection of fluoride by utilizing the empty p orbital on the boron center [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. Yamaguchi et al firstly reported the colorimetric fluoride ion sensing of triarylboron [11][12][13].…”

Ratiometric fluorescence signalling of fluoride ions by an amidophthalimide derivative

“…[25][26][27][28][29][30][31][32][33][34][35][36][37][38] However, for most of the reported fluoride sensors, the binding of the anion causes quenching of the fluorescence intensity. 34,35 Only a few sensors show guest-induced enhancement of the fluorescence intensity. 36,37 In this context, it is important to note that single wavelength intensity-based fluoresensors suffer from a number of poorly quantified factors due to the fluctuation of the excitation intensity, photobleaching, dependence of the fluorescence output on the sensor concentration etc.…”