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

Cao, Duxia; Liu, Zhi Qiang; Li, Guozhong

doi:10.1016/j.snb.2008.03.006

Cited by 27 publications

(6 citation statements)

References 36 publications

(52 reference statements)

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“…128,131,159,162 In addition to dual emission fluorescence, the amine/borane conjugates 106 and 107 have been shown to exhibit two- photon excited fluorescence (TPEF). 163,164 While the singlephoton excited fluorescence (SPEF) spectra of these molecules all display quenching of a CT emission band and appearance of a π-π* fluorescence band upon fluoride binding, the TPEF spectra display only a single emission band, which is quenched upon addition of the anion. Improvement in the TPEF properties can also be achieved by enhancing the two-photon absorption cross-section of the chromophore.…”

Section: Fluorescence Responsementioning

confidence: 99%

Fluoride Ion Complexation and Sensing Using Organoboron Compounds

et al. 2010

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Section: Fluorescence Responsementioning

confidence: 99%

Fluoride Ion Complexation and Sensing Using Organoboron Compounds

et al. 2010

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“…Triarylboranes have received much attention in the context of fluoride sensing in recent years, − but also their possible application as light-emitting materials or as electron-deficient π-conjugated units of conducting polymers has stimulated much work. − One branch of research in this multifaceted area deals with intramolecular charge transfer between electron-rich triarylamine groups and electron-poor triarylborane moieties. − In systems with π-conjugated bridges, amine-to-borane charge transfer commonly manifests as an absorption band in the electronic (UV–vis) spectrum. ,− ,− There have been recent studies of triarylborane-containing dithienylethenes, , but we are unaware of prior investigations of triarylamine–triarylborane donor–acceptor systems with photochromic bridges.…”

Section: Introductionmentioning

confidence: 99%

A Triarylamine–Triarylborane Dyad with a Photochromic Dithienylethene Bridge

Mengel

Wenger

2012

J. Org. Chem.

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A molecular triad composed of a triarylamine donor, a triarylborane acceptor, and a photoisomerizable dithienylethene bridge has been synthesized and explored by cyclic voltammetry, UV-vis, and luminescence spectroscopy. The effects of irradiation with UV light and fluoride addition on the electrochemical and optical spectroscopic properties of the donor-bridge-acceptor molecule were investigated. Photoisomerization of the dithienylethene bridge affects the triarylboron reduction potential, but not the triarylamine oxidation potential. UV-vis experiments reveal that the association constant for fluoride binding at the triarylborane site is independent of the isomerization state of the bridge. Irradiation of a THF solution of our donor-bridge-acceptor molecule with UV light, followed by F(-) addition, leads to a different color of the sample than UV irradiation alone or F(-) addition alone.

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“…Since Yamaguchi et al rst reported the uoride ion sensing of trianthrylborane, 20,21 several researchers have extended and reinforced this research. [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] Gabbaï et al successfully chelated cationic arylborane-based F À probes that can tolerate aqueous media. [22][23][24] Wang et al demonstrated an N-p-B charge-transfer system with a uorescent signal-on feature.…”

Section: Introductionmentioning

confidence: 99%

“…However, either low emission efficiency or complex molecular design limits the application of most of these probes. 35 Furthermore, these probes were mostly designed based on single-photon (SP) uorescence technology, which has relatively low signal/ noise ratios and strong photobleaching. Compared with SP uorescence, two-photon (TP) uorescence excited by simultaneously absorbing two long-wavelength photons through a virtual state offers intrinsic high three-dimensional resolution, increased penetration depth, reduced photodamage, and selfabsorption.…”

Section: Introductionmentioning

confidence: 99%

Truxene-cored π-expanded triarylborane dyes as single- and two-photon fluorescent probes for fluoride

Yuan

Wang

et al. 2014

Analyst

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Fluoride anion (F(-)) significantly affects chemical, biological, and environmental processes. Fluoride recognition and detection have received increasing attention. Convenient, effective, and sensitive fluorescent probes for F(-) should urgently be designed and synthesized. In this study, we describe a strategy for constructing two triarylborane-based fluoride fluorescent probes: 2,7,12-tri(2-(5-(dimesitylboryl)thiophen-2-yl)ethynyl)-5,5',10,10',15,15'-hexaethyltruxene (C3B3) with π-3A (acceptor) configuration and 2,7-di(N,N-diphenylamino)-12-(5-(dimesitylboryl)thiophen-2-yl)-5,5',10,10',15,15'-hexaethyltruxene (N2SB) with 2D (donor)-π-A configuration. The loss of color of the tetrahydrofuran solution of these probes from greenish yellow suggests that they can conveniently monitor F(-) at a low concentration (10 μM) free of apparatus. The different structural features of these probes varied their fluorescent responses to F(-). The single-photon fluorescence intensity of C3B3 declined to 90% upon the addition of 4.5 equivalents of F(-) to its tetrahydrofuran solution. However, the single-photon fluorescence intensity of N2SB was enhanced six-fold upon addition of 2.5 equivalents of the F(-). Under the experimental conditions, the detection limits of the two probes for F(-) can reach 12-13 μM (C3B3) and 3-5 μM (N2SB). The ability of the two probes in detecting F(-) in their toluene solutions in the two-photon mode was also investigated. The sensitive two-photon fluorescence responses of both probes make them excellent two-photon fluorescence probes.

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

Cited by 27 publications

References 36 publications

Fluoride Ion Complexation and Sensing Using Organoboron Compounds

Fluoride Ion Complexation and Sensing Using Organoboron Compounds

A Triarylamine–Triarylborane Dyad with a Photochromic Dithienylethene Bridge

Truxene-cored π-expanded triarylborane dyes as single- and two-photon fluorescent probes for fluoride

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