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

King Abdullah University of Science and Technology

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

12 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)
Pages (from-to)	2000312
Journal	Advanced Electronic Materials
DOIs	https://doi.org/10.1002/aelm.202000312
State	Published - Jun 23 2020

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10.1002/aelm.202000312

https://repository.kaust.edu.sa/bitstream/10754/663896/1/aelm.202000312.pdf

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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, 2000312. https://doi.org/10.1002/aelm.202000312

@article{bd6b6b441b4e43099f7eb6de5b1011af,

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.",

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",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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 Sk{\l}odowska-Curie Actions Innovative Training Networks “H2020-MSCA-ITN-2014 INFORM-675867” for funding.",

year = "2020",

month = jun,

day = "23",

doi = "10.1002/aelm.202000312",

language = "English (US)",

pages = "2000312",

journal = "Advanced Electronic Materials",

issn = "2199-160X",

publisher = "Wiley",

}

TY - JOUR

T1 - Correlating the Structural and Photophysical Properties of Ortho , Meta , and Para -Carboranyl–Anthracene Dyads

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 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2020/6/23

Y1 - 2020/6/23

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.

UR - http://hdl.handle.net/10754/663896

UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/aelm.202000312

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U2 - 10.1002/aelm.202000312

DO - 10.1002/aelm.202000312

M3 - Article

SN - 2199-160X

SP - 2000312

JO - Advanced Electronic Materials

JF - Advanced Electronic Materials

ER -

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

Abstract

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