Highly Efficient Far Red/Near‐Infrared Solid Fluorophores: Aggregation‐Induced Emission, Intramolecular Charge Transfer, Twisted Molecular Conformation, and Bioimaging Applications

Lu, Hongguang; Zheng, Yadan; Zhao, Xiaowei; Wang, Limin; Ma, Suqian; Han, Xiongqi; Xu, Bin; Tian, Wenjing; Gao, Hui

doi:10.1002/anie.201507031

Cited by 263 publications

(111 citation statements)

References 35 publications

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“…Interestingly, materials that exhibit luminescence in the solid state but not in solution have been known for more than a century, [2] as Sir George Stokes reported observations on platinocyanides that emit a "brilliant green" in the solid state but in solution "look like mere water". [4] Since 2001, there have been an astounding number of molecules and polymers developed that exhibit aggregation induced emission, and the resulting AIEgens have found applications in bioimaging, [5] explosives detection, [6] fingerprint visualization, [7] and in OLEDs. [3] Furthermore Tang's study of 1-methyl-1,2,3,4,5pentaphenylsilole [Ph(Me)SiC 4 Ph 4 ], which displays strong fluorescence in the solid state but only extremely weak emission in solution, set the stage for a resurgence in activity in this field.…”

Section: Introductionmentioning

confidence: 99%

Aggregation Induced Phosphorescence in the Main Group

Parke

Rivard

2018

Israel Journal of Chemistry

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This review summarizes recent progress involving the preparation of materials that exhibit aggregation induced phosphorescence (AIP) and crystallization enhanced phosphorescence, with a focus on compounds containing p‐block (main group) and Group 12 elements as active components. As will be seen, utilizing the heavy atom effect is one of the most reliable paths for unlocking phosphorescence within the main group. The vast majority of phosphorescent emitters depend on expensive transition metals, however the incorporation of main group elements in phosphors can also give rise to high luminescence quantum efficiencies at a decreased cost.

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Section: Introductionmentioning

confidence: 99%

Aggregation Induced Phosphorescence in the Main Group

Parke

Rivard

2018

Israel Journal of Chemistry

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“…Understanding the structure-property relationship is very important to guide the design of correct molecules for their providential applications1617181920212223. Artful molecular design through varying molecular backbone substituent groups and effective π-conjugation lengths or impacting the intra/intermolecular interactions to achieve high emission in the solid state is the most common method2425262728. In contrast the notorious aggregation-caused quenching (ACQ), branchy and twisted aggregation-induced emission (AIE) and aggregation-induced emission enhancement (AIEE) fluorogens are developed to tune the intermolecular stacking for efficient emissions in the solid state29303132.…”

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confidence: 99%

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Zhang

Kong

et al. 2016

Sci Rep

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Molecular packing arrangements play a key role in dominating the photophysical properties of luminophores in aggregated state but fine control of the molecular packing is a great challenge. This article describes a unique cyano substituted styrene pyridinium with interesting solid-state fluorescence that can be finely tuned by simple change of counteranions. The dilute solutions of the organic salts (PyCl, PyNO3, PyOTs and PyPh4B) exhibit very weak fluorescence. The crystals of the organic salts (PyCl, PyNO3, and PyOTs) show much enhanced fluorescence compared with their dilute solutions. It is interesting that the emissions changed from bluish-green to deep-blue and fluorescence quantum yields increase from 2.5% to 13.1% with the increasing of steric hindrance of the anions from chloridion, nitrate, to p-toluenesulfonate. Crystal and DFT studies reveal that the enhanced fluorescence is ascribed to the formation of dimers and bigger anions induce larger molecular separation in dimers. Tetraphenylboron anion with very large steric hindrance impedes the formation of dimers and thus results in non-fluorescent salt (PyPh4B). Meanwhile, this unique dimeric packing endows the crystal of PyNO3 with anisotropic fluorescence.

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“…For some applications, the emission in neat or aggregate state is a basic requirement. This is the case in most optoelectronic devices and in fluorescent bioimaging investigation techniques [5][6][7][8]. In the organic fluorophores, traditionally consisting of extended electronic π-systems, a marked fluorescence quenching in the solid state can occur due to the strong intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

et al. 2020

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We developed a new benzodifuran derivative as the condensation product between 2,6-diamino -4-(4-nitrophenyl)benzo [1,2-b:4,5-b']difuran-3,7-dicarboxylate and 3-hydroxy-2-naphthaldehyde. The intramolecular hydrogen-bond interactions in the terminal half-salen moieties produce a sterically encumbered highly conjugated main plane and a D-A-D (donor-acceptor-donor) T-shaped structure. The novel AIEgen (aggregation-induced enhanced emission generator) fulfils the requirement of RIR (restriction of intramolecular rotation) molecules. DR/NIR (deep red/near infrared) emission was recorded in solution and in the solid state, with a noteworthy photoluminescence quantum yield recorded on the neat crystals which undergo some mechanochromism. The crystal structure study of the probe from data collected at a synchrotron X-ray source shows a main aromatic plane π-stacked in a columnar arrangement.Crystals 2020, 10, 269 2 of 15 law [20][21][22] the intrinsic low band-gap of such DR/NIR emitters makes them especially vulnerable to the ACQ effect [23] due to higher vibrionic coupling between the ground and excited states. Therefore, most of the AIEgens reported emit blue and green lights. Although they are highly sought after for red OLEDs (Organic Light Emitting Diodes), night-vision devices, secured displays, optical waveguides and in the wide field of bio and chemo-sensing [24][25][26][27][28], there are fewer efficient DR/NIR (deep red/near infrared) materials. Of particular interest are AIE fluorophores with intense emission at DR/NIR region owing to their deep tissue penetration, photo-stability and minimum interference in living systems [25,29,30]. Their applications are closely related to cell imaging and DNA and protein sensing [31][32][33].Novel molecular construction of DR/NIR AIEgens can be achieved with electron donor (D) and electron acceptor (A) blocks connected through π-conjugated frameworks. The most fundamental phenomenon governing the spectroscopic properties is the intramolecular charge transfer (ICT) process from the donor to the acceptor in the excited state [34][35][36]. Intercrossed excited state between the low-lying local exciton (LE) and charge transfer (CT) exciton results from the D-A interaction. Obviously, the molecular geometry is crucial for the process.Benzodifuran derivatives have drawn attention for a wide range of biological and pharmacological applications, including antimicrobial, antiviral, analgesic and antitumor [37][38][39][40] activity. This class of heterocyclic compounds are also employed in dyes industry as pigments and in different fields of optoelectronics and photonics. Due to the excellent semiconducting properties [41,42], benzodifuran scaffolds are used as nonlinear optical materials [43], for dye sensitized solar cells [44] and in organic solar cell and transistors. Finally, as electron-rich building blocks they have a potential in the constructing of photoluminescent materials [45][46][47] Herein, we developed a new benzodifuran derivative from 2,6-diamino-4-(4-nitrophenyl) ...

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Highly Efficient Far Red/Near‐Infrared Solid Fluorophores: Aggregation‐Induced Emission, Intramolecular Charge Transfer, Twisted Molecular Conformation, and Bioimaging Applications

Cited by 263 publications

References 35 publications

Aggregation Induced Phosphorescence in the Main Group

Aggregation Induced Phosphorescence in the Main Group

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

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