Multifunctional luminescent molecules of o -carborane-pyrene dyad/triad: flexible synthesis and study of the photophysical properties

Wu, Xueyan; Guo, Jixi; Zhao, Jianzhang; Che, Yuanyuan; Jia, Dianzeng; Chen, Yi

doi:10.1016/j.dyepig.2018.02.035

Cited by 42 publications

(41 citation statements)

References 57 publications

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“…[37] Accordingly,t hese data indicatet hat the luminescent band at % 400 nm for Py-NC should be assigned to the locally excited state. [17] Regarding Au I complexes 1 and 2,s imilar absorption was observed in solvents with different polarities, except for in DMF. In contrast, the emission spectra of these two gold(I) complexes show relatively obviouss olventp olarity dependence.…”

Section: Photophysical Properties and Dft Calculationmentioning

confidence: 82%

“…Pyrene derivatives featuring AIE have been widely reported in recent years. [17,18] In contrast, pyrene-based AIE compounds that achievem onomer-excimerc onversion in solution are less frequently reported [19] and somed erivatives are documented to exhibit both monomeric and excimer emission in solution, allowing their use as fluorescent probesa nd highlys ensitive fluorescent sensors. [14,[20][21][22][23] Regarding the emission in the solid state, variousk inds of mechanochromic illuminants based on pyrene derivates have been reported, which are accompanied by excimer-to-excimer,m onomer-to-excimer and conformation transitions.…”

Section: Introductionmentioning

confidence: 99%

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Multiple Photoluminescent Processes from Pyrene Derivatives with Aggregation‐ and Mechano‐Induced Excimer Emission

Wang

Zhang

Yin

et al. 2019

Chemistry An Asian Journal

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Twon ovel pyrene-based isocyanide gold(I)c omplexes have been designed and synthesized.T he different structures lead to distinct and diverse photophysical properties both in solution and in the aggregate state. Multiple photoluminescence, involving monomer emission, locally ex-cited emission and excimer emission, are observed. Notably, an excimer is formed by aggregation in solution and external mechanical stimulation in the solid state, showing aggregation-and mechano-induced excimer emission.Figure 1. Molecule structureo fPy-NC, 1 and 2.[a] Dr.

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Section: Photophysical Properties and Dft Calculationmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Multiple Photoluminescent Processes from Pyrene Derivatives with Aggregation‐ and Mechano‐Induced Excimer Emission

Wang

Zhang

Yin

et al. 2019

Chemistry An Asian Journal

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“…Other types of AIE‐active o ‐carborane derivatives are listed in Table and Scheme . Influences on AIE properties were investigated by changing the substituents on the o ‐carborane unit ( 44 – 75 ) . For these compounds, solid‐state excimer emission, single‐molecule white emission, aggregation‐induced electrochemiluminescence, and thermally activated delayed fluorescence were observed.…”

Section: Aggregation‐induced Emissionmentioning

confidence: 99%

Recent Progress in the Development of Solid‐State Luminescent o‐Carboranes with Stimuli Responsivity

2020

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o‐Carborane, a cluster compound containing boron and adjacent carbon atoms, displays intriguing luminescent properties. Recently, compounds containing o‐carborane units were found to show suppressed aggregation‐induced quenching and intense solid‐state emission; they also show potential for the development of stimuli‐responsive luminochromic materials. In this Minireview, we introduce three kinds of fundamental photochemical properties: aggregation‐induced emission, twisted intramolecular charge transfer in crystals, and environment‐sensitive excimer formation in solids. Based on these properties, several types of luminochromism, such as thermos‐, vapo‐, and mechanochromism, have been discovered. Based mainly on results from recent studies, we illustrate these mechanisms as well as unique luminescent behaviors of o‐carborane derivatives.

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“…[19,20,23] In these few cases,h owever, the carborane can be considered essentially electronically isolated from the aromatic excimer species,s ave for some electron-withdrawing inductive effects.…”

mentioning

confidence: 99%

“…[27] In other cases where o-carborane has been attached to pyrene,t he bulky carborane moiety was found not to inhibit the p-p stacking required for pyrene excimer formation. [19,20,23] In these few cases,h owever, the carborane can be considered essentially electronically isolated from the aromatic excimer species,s ave for some electron-withdrawing inductive effects.…”

mentioning

confidence: 99%

Carborane‐Induced Excimer Emission of Severely Twisted Bis‐o‐Carboranyl Chrysene

et al. 2018

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The synthesis of ahighly twisted chrysenederivative incorporating two electron deficient o-carboranyl groups is reported. The molecule exhibits ac omplex, excitation-dependent photoluminescence,i ncluding aggregation-induced emission (AIE) with good quantum efficiency and an exceptionally long singlet excited state lifetime.T hrough ac ombination of detailed optical studies and theoretical calculations,the excited state species are identified, including an unusual excimer induced by the presence of o-carborane.T his is the first time that o-carborane has been shown to induce excimer formation ab initio,aswell as the first observation of excimer emission by achrysene-based small molecule in solution. Bis-o-carboranyl chrysene is thus an initial member of an ew family of ocarboranyl phenacenes exhibiting an ovel architecture for highly-efficient multi-luminescent fluorophores.Atfirst glance,b ulky boron-rich spheroids appear to be an anathema to the two-dimensional, p-conjugated world of organic electronics.O nt he contrary,m otivated by their unique three-dimensional s-delocalization, electron-withdrawing ability (when substituted at the carbon vertices), [1] and high thermal and chemical stability,c arboranes,a nd principally o-carborane (C 2 B 10 H 12 ), have now been incorporated in aw ide range of molecular and polymeric semiconductors. Ak ey property of o-carborane is its ability to accept an excited charge via intramolecular charge transfer (ICT) from an aryl donor group,o ccurring most efficiently when the carborane has its C À Cb ond perpendicular to the aromatic plane.T hese ICT states are notable for their flexible carboranyl CÀCb ond, which can vibrate and relax nonradiatively,o rr adiatively with ah ighly red-shifted emission. [24][25][26][27][28][29][30] Such systems often exhibit aggregation-induced emission (AIE), [13-15,17-20, 22, 31, 32] that is,i na na ggregated state where molecular motion is restricted, non-radiative relaxation pathways from the ICT state are inhibited, leading to as ignificant increase in emission efficiency. It has been demonstrated that incorporation of bulky carboranes on the long edges of linear acenes creates al arge steric hinderance between the carboranes and proximal protons,l eading to aconsiderable deformation of the ring system. [15][16][17] With this comes alarge increase in the carborane rotation barrier, and generally am ore rigid structure;aproperty known to be useful for AIE.o-Carborane has also been shown, to av ery limited extent, to aid excimer emission. When di-substituted with two naphthyl donor groups,t he imposed proximity of the aryl systems allows for an overlap of the aromatic wavefunctions, such that dimerization occurs readily when one naphthalene is in the excited state.[27] In other cases where o-carborane has been attached to pyrene,t he bulky carborane moiety was found not to inhibit the p-p stacking required for pyrene excimer formation. [19,20,23] In these few cases,h owever, the carborane can be considered essentially electronica...

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Multifunctional luminescent molecules of o -carborane-pyrene dyad/triad: flexible synthesis and study of the photophysical properties

Cited by 42 publications

References 57 publications

Multiple Photoluminescent Processes from Pyrene Derivatives with Aggregation‐ and Mechano‐Induced Excimer Emission

Multiple Photoluminescent Processes from Pyrene Derivatives with Aggregation‐ and Mechano‐Induced Excimer Emission

Recent Progress in the Development of Solid‐State Luminescent o‐Carboranes with Stimuli Responsivity

Carborane‐Induced Excimer Emission of Severely Twisted Bis‐o‐Carboranyl Chrysene

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