Boranil dyes bearing tetraphenylethene: Synthesis, AIE/AIEE effect properties, pH sensitive properties and application in live cell imaging

Chen, Shengxin; Qiu, Rongmao; Yu, Qiuhan; zhang, Xueyan; Wei, Ming; Dai, Zhenya

doi:10.1016/j.tetlet.2018.05.081

Cited by 19 publications

(7 citation statements)

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“…An important feature of such boron(III)-chelated dyes is their facile transformation into other derivatives, which includes attachment of disparate groups at either end of the molecular framework. Preliminary reports of the photophysical properties of certain boranil derivatives in fluid solution , appear consistent with intramolecular charge-transfer character . Thus, fluorescence quantum yields decrease with increasing solvent polarity and there are accompanying solvent-imposed effects on the spectral properties and Stokes shifts.…”

Section: Introductionmentioning

confidence: 56%

“…Preliminary reports of the photophysical properties of certain boranil derivatives in fluid solution 15,18 appear consistent with intramolecular charge-transfer character. 19 Thus, fluorescence quantum yields decrease with increasing solvent polarity and there are accompanying solvent-imposed effects on the spectral properties and Stokes shifts. In the reported cases, fluorescence is significant only in nonpolar or weakly polar media.…”

Section: ■ Introductionmentioning

confidence: 99%

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Origin of Fluorescence from Boranils in the Crystalline Phase

et al. 2020

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A small series of boranil complexes has been studied by fluorescence spectroscopy. Weakly fluorescent in most organic solvents at room temperature, the target compounds display bright emission in the crystalline phase. X-ray diffraction patterns obtained for single crystals indicate a distorted tetrahedral geometry around the O–B–N center with the boron atom being displaced from the plane of the heterobicyclic ring. Consideration of the various bond lengths in comparison with those of reference compounds indicates that the ancillary phenyl ring, bearing different para-substituents, does not make a prominent contribution to the molecular dipole moment in the solid state. Absorption and fluorescence spectra recorded for the crystals remain remarkably similar to those for liquid solutions and display large Stokes shifts. Proximity broadening is observed in one case. The nitrophenyl derivative exhibits additional absorption and emission bands unique to the solid state and could be indicative of an intermolecular charge-transfer transition. The optical properties are discussed in terms of the crystal packing diagrams.

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Section: Introductionmentioning

confidence: 56%

Section: ■ Introductionmentioning

confidence: 99%

Origin of Fluorescence from Boranils in the Crystalline Phase

et al. 2020

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“…The fluorescence intensity was greatly enhanced when the compound aggregated. 32 PBAQA has a strong fluorescence in methanol and the fluorescence intensity did not change much with the change of water content. When the water content exceeded 50%, the fluorescence intensity decreased (Figure 3(a)).…”

Section: Resultsmentioning

confidence: 91%

“…Subsequently, this phenomenon was named aggregation-induced emission (AIE). 14,15 The restriction of intramolecular rotation (RIR) was identified as the main cause for enhancing the fluorescence. 16 When dissolved in a suitable solvent, the benzene ring undergoes intramolecular rotation with its single bond between the other rings as an axis, consuming excitation energy.…”

Section: Introductionmentioning

confidence: 99%

2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

Fang

Wang

Bian

et al. 2019

Journal of Chemical Research

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Long-wavelength fluorescent sensors with large Stokes shifts show useful applications in chemical biology and clinical laboratory diagnosis. We have recently reported [4-(4-{[3-(4-boronobenzamido)propyl]carbamoyl}quinolin-2-yl)phenyl]boronic acid that can selectively recognize d-ribose in a buffer solution of pH 7.4. However, the short emission wavelength (395 nm) and aggregation-caused quenching effect are not conducive to applications as a sensor. Novel diboronic acid compounds are synthesized using 2-(4-boronophenyl)quinoline-4-carboxylic acid as the building block and p-phenylenediamine as the linker. These compounds show aggregation-induced emission and fluorescence emission at about 500 nm. In addition, after binding to most carbohydrates, the aggregated state of the boronic acid–containing compounds is dissociated, resulting in fluorescence quenching. Using [4-(4-{[4-(3-borono-5-methoxybenzamido)phenyl]carbamoyl}quinoline-2-yl)phenyl]boronic acid as an example, addition of 55 mM of d-ribose resulted in the strongest quenching of 83% for all the tested carbohydrates, indicating selectively recognizing d-ribose. The reciprocal of the fluorescence intensity change showed a good linear relationship with the reciprocal of d-ribose concentration ( R2 ⩾ 0.99), indicating sensor binding to d-ribose in a ratio of 1:1 to form an inclusion complex. The fluorescence emission is red-shifted compared to 2-(4-boronophenyl)quinoline-4-carboxylic acid and its common derivatives, which provides a new method for the development of long-wavelength fluorescent sensors.

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“…In 2001, Tang and co-workers observed an uncommon and unconventional phenomenon in which some compounds with unique structures are almost non-fluorescent when dissolved in an organic solvent, but which become highly emissive in the aggregate state, a process known as aggregation-induced emission (AIE) or aggregation-induced emission enhancement (AIEE). 7 It is promising that AIE compounds not only solve the aggregation-induced quenching (ACQ) problem without causing any adverse effects, 8,9 but are also stable and highly selective fluorescent sensors for proteins, 10,11 DNA, 12 sugars, 13 metal ions, 14,15 biological anions, 16 cyanide detection, 17 drug carriers, 18 cell imaging, 19,20 and explosive detection. 21,22 According to recent research achievements related to chiral recognition, the conclusion is that there is a simple and effective method to obtain excellent chiral sensors via the combination of one molecule having AIE character with another molecule having a chiral center.…”

Section: Introductionmentioning

confidence: 99%