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 (Corresponding author)

Research output: Contribution to journal › Article › Academic › peer-review

23 Citations (Scopus)

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
Article number	2000312
Number of pages	7
Journal	Advanced Electronic Materials
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/aelm.202000312
Publication status	Published - 1 Aug 2020

Funding

The authors thank the EPRSC for funding (EP/G037515/1 & EP/ L016702/1) and AWE for their input and financial support of A.V.M. The authors also thank the Marie Skłodowska‐Curie Actions Innovative Training Networks “H2020‐MSCA‐ITN‐2014 INFORM‐675867” for funding.

Funders	Funder number
European Union's Horizon 2020 - Research and Innovation Framework Programme	675867
Atomic Weapons Establishment	H2020-MSCA-ITN-2014 INFORM-675867

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.",

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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.

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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.

KW - carborane

KW - organic optoelectronics

KW - organic semiconductors

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ER -

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

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Keywords

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