Aggregation‐Induced Emission and Efficient Solid‐State Fluorescence from Tetraphenylethene‐Based N,C‐Chelate Four‐Coordinate Organoborons

Zhao, Zujin; Chang, Zhengfeng; He, Bo; Chen, Bin; Deng, Chunmei; Lü, Ping; Qiu, Huayu; Tang, Ben Zhong

doi:10.1002/chem.201301815

Cited by 91 publications

(22 citation statements)

References 62 publications

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“…Catalytic turnover proceeded effectively at raised temperatures down to catalyst loadings of 5 mol% HNTf 2 . Since Vedejs and co-worker's seminal report in 2009, a number of other intramolecular borylations have been reported where borocations have been proposed as intermediates; this includes pyridyl- [50][51][52] and phosphinite [53]-directed dehydroborations. In the pyridyl-directed borylation, excess BBr 3 and the hindered base, NEt i Pr 2 , were both essential; the base required either to deprotonate an arenium intermediate if the reaction proceeds by an S E Ar mechanism or sequester HBr to prevent protodeboronation.…”

Section: Intramolecular Electrophilic Aromatic Borylationmentioning

confidence: 97%

Fundamental and Applied Properties of Borocations

Ingleson

2015

Synthesis and Application of Organoboron Compounds

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Section: Intramolecular Electrophilic Aromatic Borylationmentioning

confidence: 97%

Fundamental and Applied Properties of Borocations

Ingleson

2015

Synthesis and Application of Organoboron Compounds

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“…[6] Prominent examples are boron 8-hydroxyquinolinate complexes, [7,8] boron dipyrromethene (Bodipy) dyes, [9][10][11] boranils, [12,13] and boron iminocoumarins (Boricos). [14] To a lesser extent organoboron complexes with N,C-chelate systems were reported, [15][16][17][18][19] B(ppy)Mes2 compounds (ppy = 2-phenylpyridyl, Mes = mesityl) being an example. [20] Interestingly, some of the latter were shown to feature reversible photochromic behaviour.…”

Section: Introductionmentioning

confidence: 99%

Strongly Emissive and Photostable Four‐Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

Pais

Alcaide

López‐Rodríguez

et al. 2015

Chemistry A European J

112

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Six strongly fluorescent four-coordinate organoboron N,Cchelates, containing an arylisoquinoline skeleton, were prepared. Remarkably, the fluorescence quantum yields reach values of up to 0.74 in oxygen-free toluene. The strong B-N interaction was corroborated by the single-crystal X-ray analysis of two dyes. The intramolecular charge-transfer (ICT) character of the fluorophores was evidenced by solvatochromic studies and time-dependent density-functional-theory calculations at the PCM(toluene)/CAM-B3LYP/6-311++G(2d,p)//PCM(toluene)/B3LYP/6-311G(2d,p) level of theory. The compounds combine high chemical stability with high photostability (especially when equipped with electron-donating substituents). The strong fluorescence and the large Stokes shifts predestine these compounds for their use in confocal fluorescence microscopy. This was demonstrated for the imaging of the N13 mouse microgial cell line. As a surplus, significant two-photon absorption cross sections (up to 61 GM) allow the use of excitation wavelengths in the near-infrared region (> 800 nm).

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“…Among the diverse strategies developed to mitigate the ACQ effect, the utilization of small molecules experiencing the so called aggregation‐induced emission (AIE) phenomenon proposed by Tang and co‐workers has been identified as an emerging and successful approach. This phenomenon is observed for some molecules that are nonemissive or weakly fluorescent molecules in dilute solutions and upon aggregation do not achieve a sandwich packing.…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembling Azaindole Organogel for Organic Light‐Emitting Devices (OLEDs)

Martín

Kennes

Auweraer

et al. 2017

Adv Funct Materials

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This study reports on the use of a self-assembling organogel, 5-(4-nonylphenyl)-7-azaindole (1), as a new emitter in small-molecule organic light emitting devices (OLEDs). The theoretical calculations along with the photophysical characterization studies suggest the coexistence of the monomer and dimer species at high concentration of compound 1. The presence of this type of dimer (formed via H-bonding) is responsible for the increased emission. However, the most notable feature is the 3D network of vastly interconnected fibers formed in the organogel that modifies the photophysical properties. Based on this, several OLED architectures are made in order to understand the mechanism involved in the electroluminescence (EL) behavior of 1. Although the position of the EL spectra differs from that of the photoluminescence (PL) spectra, the trends observed in the device properties perfectly match with dimer formation. In this framework a better device performance is associated to a higher efficiency of dimer formation, which optimizes in the OLED prepared from the organogel. Therefore, these results show that the rational combination of a moiety showing a strong PL intensity increased upon aggregation with organogel properties is an efficient strategy to create alternative emitters for OLED devices.

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Aggregation‐Induced Emission and Efficient Solid‐State Fluorescence from Tetraphenylethene‐Based N,C‐Chelate Four‐Coordinate Organoborons

Cited by 91 publications

References 62 publications

Fundamental and Applied Properties of Borocations

Fundamental and Applied Properties of Borocations

Strongly Emissive and Photostable Four‐Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

Self‐Assembling Azaindole Organogel for Organic Light‐Emitting Devices (OLEDs)

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