Synthesis, aggregation-induced emission and mechanochromism of a new carborane-tetraphenylethylene hybrid

Nie, Yong; Zhang, Hao; Miao, Junjie; Xin, Zhao; Li, Yexin; Sun, Guangmin

doi:10.1016/j.jorganchem.2018.03.034

Cited by 18 publications

(15 citation statements)

References 33 publications

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“…described the bis(naphthyl)phenyl‐substituted carborane 85 , which showed a bathochromic shift by 14 nm upon grinding and presented green fluorescence . They also reported the mechanochromic luminescent compound 24 containing a TPE moiety . Huang et al.…”

Section: Mechanochromic Luminescencesupporting

confidence: 61%

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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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Section: Mechanochromic Luminescencesupporting

confidence: 61%

“…Another type of TPE substituent containing a stilbene linker is found in 22 and 23 , which were synthesized by Núñez and co‐workers . Some other TPE derivatives showed luminescence color changes upon application of mechanical force ( 19 , 24 ) . They will be discussed later in Section 5.…”

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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“…Charge transfer has been shown to occur preferentially when the carboranyl carbon–carbon (C C −C C ) bond is perpendicular to plane of the donor fluorophore and, structurally, this state is notable for an elongated carborane C C −C C bond [17] . In good solvents, these ICT states are very weakly emissive, as vibration of the C C −C C bond acts as a non‐radiative decay pathway for the excited state [18–22] . Whenever molecular motion is restricted, however, carboranyl ICT states become more radiative.…”

Section: Figurementioning

confidence: 99%

“…Whenever molecular motion is restricted, however, carboranyl ICT states become more radiative. This often occurs upon aggregation, in a process known as aggregation induced emission (AIE) [7, 17, 18, 20–39] . o ‐Carborane is therefore considered an ‘AIE‐active element block’ [40]…”

Section: Figurementioning

confidence: 99%

“…[17] In good solvents, these ICT states are very weakly emissive, as vibration of the C C ÀC C bond acts as an on-radiatived ecay pathway for the excited state. [18][19][20][21][22] Whenevermolecular motion is restricted, however,c arboranyl ICT states become more radiative. This often occurs upon aggregation,i naprocess knowna sa ggregationi nduced emission (AIE).…”

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confidence: 99%

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Highly Deformedo‐Carborane Functionalised Non‐linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

Marsh

Little

Cheetham

et al. 2020

Chemistry A European J

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The effect of substituting o‐carborane into the most sterically hindered positions of phenanthrene and benzo(k)tetraphene is reported. Synthesised via a Bull–Hutchings–Quayle benzannulation, the crystal structures of these non‐linear acenes exhibited the highest aromatic deformation parameters observed for any reported carborane compound to date, and among the largest carboranyl C−C bond length of all organo‐substituted o‐carboranes. Photoluminescence studies of these compounds demonstrated efficient intramolecular charge‐transfer, leading to aggregation induced emission properties. Additionally, an unusual low‐energy excimer was observed for the phenanthryl compound. These are two new members of the family of carborane‐functionalised non‐linear acenes, notable for their peculiar structures and multi‐luminescent properties.

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Correlating the Structural and Photophysical Properties of Ortho, Meta, and Para‐Carboranyl–Anthracene Dyads

Marsh

Dyson

Cheetham

et al. 2020

Adv Elect Materials

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The role of the carborane isomer is investigated on the structural and photophysical properties of molecules comprising a carborane cluster and a conjugated organic moiety is investigated by synthesizing isomeric o‐, m‐, and p‐carboranyl‐anthracene donor–acceptor dyads. While appending a carborane leads to emission from a low energy intramolecular charge transfer state for the o‐isomer, as well as emission from an excited state localized on the anthracene, this is not the case for the m‐ and p‐carborane derivatives. This difference is attributed to a lower electron affinity for the latter two isomers. However, adding both m‐ and p‐ deforms the aromatic backbone and increases its structural rigidity, reducing non‐radiative decay pathways and hence enhancing photoluminescence quantum efficiency relative to anthracene.

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Synthesis, aggregation-induced emission and mechanochromism of a new carborane-tetraphenylethylene hybrid

Cited by 18 publications

References 33 publications

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

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

Highly Deformedo‐Carborane Functionalised Non‐linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

Correlating the Structural and Photophysical Properties of Ortho, Meta, and Para‐Carboranyl–Anthracene Dyads

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