Tyrian purple: an ancient natural dye for cross-conjugated n-type charge transport

Kealan J. Fallon; Nilushi Wijeyasinghe; Anastasia Leventis; Jose M. Marin-Beloqui; Daniel T. W. Toolan; Mohammed Al-Hashimi; Tracey M. Clarke; Thomas D. Anthopoulos; Hugo Bronstein

doi:10.1039/d0tc05553k

Tyrian purple: an ancient natural dye for cross-conjugated n-type charge transport

Kealan J. Fallon, Nilushi Wijeyasinghe, Anastasia Leventis, Jose M. Marin-Beloqui, Daniel T. W. Toolan, Mohammed Al-Hashimi, Tracey M. Clarke, Thomas D. Anthopoulos, Hugo Bronstein

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Abstract

Herein, we present two novel organic semiconducting polymers synthesised from an ancient dye. By employing cross-conjugation within the polymer backbone as a synthetic strategy, we are able to engineer optical gaps such that the novel materials absorb over the entire visible spectrum. The cross-conjugated polymers exhibited relatively high n-type charge transport performance in organic field-effect transistors, a rare characteristic for this type of polymer. Quantum chemical calculations provide insight into this behaviour, suggesting that, whilst conjugation along the HOMO is indeed inhibited via molecular design, these materials possess highly delocalized LUMOs, facilitating high n-type charge transport.

Original language	English (US)
Journal	Journal of Materials Chemistry C
DOIs	https://doi.org/10.1039/d0tc05553k
State	Published - 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-03-10
Acknowledgements: The authors gratefully acknowledge support for this work from the Qatar National Research Fund project number: NPRP 12S-0304-190227, EU project 679789 – 455 CONTREX and the EPSRC grant EP/S003126/1.

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10.1039/d0tc05553k

https://repository.kaust.edu.sa/bitstream/10754/667985/1/d0tc05553k.pdf

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@article{959cc5a634144b11bf4bdfe1ce792fa5,

title = "Tyrian purple: an ancient natural dye for cross-conjugated n-type charge transport",

abstract = "Herein, we present two novel organic semiconducting polymers synthesised from an ancient dye. By employing cross-conjugation within the polymer backbone as a synthetic strategy, we are able to engineer optical gaps such that the novel materials absorb over the entire visible spectrum. The cross-conjugated polymers exhibited relatively high n-type charge transport performance in organic field-effect transistors, a rare characteristic for this type of polymer. Quantum chemical calculations provide insight into this behaviour, suggesting that, whilst conjugation along the HOMO is indeed inhibited via molecular design, these materials possess highly delocalized LUMOs, facilitating high n-type charge transport.",

author = "Fallon, {Kealan J.} and Nilushi Wijeyasinghe and Anastasia Leventis and Marin-Beloqui, {Jose M.} and Toolan, {Daniel T. W.} and Mohammed Al-Hashimi and Clarke, {Tracey M.} and Anthopoulos, {Thomas D.} and Hugo Bronstein",

note = "KAUST Repository Item: Exported on 2021-03-10 Acknowledgements: The authors gratefully acknowledge support for this work from the Qatar National Research Fund project number: NPRP 12S-0304-190227, EU project 679789 – 455 CONTREX and the EPSRC grant EP/S003126/1.",

year = "2021",

doi = "10.1039/d0tc05553k",

language = "English (US)",

journal = "Journal of Materials Chemistry C",

issn = "2050-7526",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Tyrian purple: an ancient natural dye for cross-conjugated n-type charge transport

AU - Fallon, Kealan J.

AU - Wijeyasinghe, Nilushi

AU - Leventis, Anastasia

AU - Marin-Beloqui, Jose M.

AU - Toolan, Daniel T. W.

AU - Al-Hashimi, Mohammed

AU - Clarke, Tracey M.

AU - Anthopoulos, Thomas D.

AU - Bronstein, Hugo

N1 - KAUST Repository Item: Exported on 2021-03-10 Acknowledgements: The authors gratefully acknowledge support for this work from the Qatar National Research Fund project number: NPRP 12S-0304-190227, EU project 679789 – 455 CONTREX and the EPSRC grant EP/S003126/1.

PY - 2021

Y1 - 2021

N2 - Herein, we present two novel organic semiconducting polymers synthesised from an ancient dye. By employing cross-conjugation within the polymer backbone as a synthetic strategy, we are able to engineer optical gaps such that the novel materials absorb over the entire visible spectrum. The cross-conjugated polymers exhibited relatively high n-type charge transport performance in organic field-effect transistors, a rare characteristic for this type of polymer. Quantum chemical calculations provide insight into this behaviour, suggesting that, whilst conjugation along the HOMO is indeed inhibited via molecular design, these materials possess highly delocalized LUMOs, facilitating high n-type charge transport.

AB - Herein, we present two novel organic semiconducting polymers synthesised from an ancient dye. By employing cross-conjugation within the polymer backbone as a synthetic strategy, we are able to engineer optical gaps such that the novel materials absorb over the entire visible spectrum. The cross-conjugated polymers exhibited relatively high n-type charge transport performance in organic field-effect transistors, a rare characteristic for this type of polymer. Quantum chemical calculations provide insight into this behaviour, suggesting that, whilst conjugation along the HOMO is indeed inhibited via molecular design, these materials possess highly delocalized LUMOs, facilitating high n-type charge transport.

UR - http://hdl.handle.net/10754/667985

UR - http://xlink.rsc.org/?DOI=D0TC05553K

U2 - 10.1039/d0tc05553k

DO - 10.1039/d0tc05553k

M3 - Article

SN - 2050-7526

JO - Journal of Materials Chemistry C

JF - Journal of Materials Chemistry C

ER -

Tyrian purple: an ancient natural dye for cross-conjugated n-type charge transport

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