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

Adam V. Marsh; Matthew J. Dyson; Nathan J. Cheetham; Matthew Bidwell; Mark Little; Andrew J.P. White; Colin N. Warriner; Anthony C. Swain; Iain McCulloch; Paul N. Stavrinou; Stefan C.J. Meskers; Martin Heeney

doi:10.1002/aelm.202000312

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

Adam V. Marsh, Matthew J. Dyson, Nathan J. Cheetham, Matthew Bidwell, Mark Little, Andrew J.P. White, Colin N. Warriner, Anthony C. Swain, Iain McCulloch, Paul N. Stavrinou, Stefan C.J. Meskers, Martin Heeney

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15 Scopus citations

Abstract

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.

Original language	English (US)
Article number	2000312
Journal	Advanced Electronic Materials
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/aelm.202000312
State	Published - Aug 1 2020
Externally published	Yes

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials

Keywords

carborane
organic optoelectronics
organic semiconductors

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10.1002/aelm.202000312

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Marsh, A. V., Dyson, M. J., Cheetham, N. J., Bidwell, M., Little, M., White, A. J. P., Warriner, C. N., Swain, A. C., McCulloch, I., Stavrinou, P. N., Meskers, S. C. J., & Heeney, M. (2020). Correlating the Structural and Photophysical Properties of Ortho, Meta, and Para-Carboranyl–Anthracene Dyads. Advanced Electronic Materials, 6(8), Article 2000312. https://doi.org/10.1002/aelm.202000312

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title = "Correlating the Structural and Photophysical Properties of Ortho, Meta, and Para-Carboranyl–Anthracene Dyads",

abstract = "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.",

keywords = "carborane, organic optoelectronics, organic semiconductors",

author = "Marsh, {Adam V.} and Dyson, {Matthew J.} and Cheetham, {Nathan J.} and Matthew Bidwell and Mark Little and White, {Andrew J.P.} and Warriner, {Colin N.} and Swain, {Anthony C.} and Iain McCulloch and Stavrinou, {Paul N.} and Meskers, {Stefan C.J.} and Martin Heeney",

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year = "2020",

month = aug,

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doi = "10.1002/aelm.202000312",

language = "English (US)",

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AU - Marsh, Adam V.

AU - Dyson, Matthew J.

AU - Cheetham, Nathan J.

AU - Bidwell, Matthew

AU - Little, Mark

AU - White, Andrew J.P.

AU - Warriner, Colin N.

AU - Swain, Anthony C.

AU - McCulloch, Iain

AU - Stavrinou, Paul N.

AU - Meskers, Stefan C.J.

AU - Heeney, Martin

N1 - Publisher Copyright: Crown Owned Copyright AWE, UK Ministry of Defence

PY - 2020/8/1

Y1 - 2020/8/1

N2 - 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.

AB - 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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KW - organic optoelectronics

KW - organic semiconductors

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

Abstract

All Science Journal Classification (ASJC) codes

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