Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

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

doi:10.1002/chem.202004517

Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

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

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

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1970-1975
Number of pages	6
Journal	Chemistry - A European Journal
Volume	27
Issue number	6
DOIs	https://doi.org/10.1002/chem.202004517
Publication status	Published - 26 Jan 2021

Funding

We thank the Engineering and Physical Sciences Research Council (EPSRC EP/L016702/1), the Royal Society and the Wolfson Foundation (Royal Society Wolfson Fellowship for funding. We also thank AWE for their input and financial support of A. V. M. We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University, and the Marie Skłodowska–Curie Actions Innovative Training Networks “H2020-MSCA-ITN-2014 INFORM -675867” for funding. This article is UK Ministry of Defence © Crown Owned Copyright 2020/AWE.

Funders	Funder number
Swansea University	675867
Marie Skłodowska‐Curie
Engineering and Physical Sciences Research Council	EP/L016702/1

Keywords

AIE
carboranes
charge transfer
fluorescence
polycyclic aromatic hydrocarbons

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10.1002/chem.202004517

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Marsh, A. V., Little, M., Cheetham, N. J., Dyson, M. J., Bidwell, M., White, A. J. P., Warriner, C. N., Swain, A. C., McCulloch, I., Stavrinou, P. N., & Heeney, M. (2021). Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds. Chemistry - A European Journal, 27(6), 1970-1975. https://doi.org/10.1002/chem.202004517

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title = "Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds",

abstract = "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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AU - Dyson, Matthew J.

AU - Bidwell, Matthew

AU - White, Andrew J.P.

AU - Warriner, Colin N.

AU - Swain, Anthony C.

AU - McCulloch, Iain

AU - Stavrinou, Paul N.

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AB - 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.

KW - AIE

KW - carboranes

KW - charge transfer

KW - fluorescence

KW - polycyclic aromatic hydrocarbons

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JO - Chemistry - A European Journal

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Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C−C Bonds

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Keywords

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