A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge

Weikang Xiao; Zhiqun He; Sonia Remiro Buenamanana; Rebecca Turner; Min Xu; Xiao Yang; Xiping Jing; Andrew N. Cammidge

doi:10.1021/acs.orglett.5b01444

A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge

Weikang Xiao, Zhiqun He (Lead Author), Sonia Remiro Buenamanana, Rebecca Turner, Min Xu, Xiao Yang, Xiping Jing, Andrew N. Cammidge (Lead Author)

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Abstract

Beta-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophe-none imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demon-strates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character

Original language	English
Pages (from-to)	3286–3289
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	13
Early online date	19 Jun 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b01444
Publication status	Published - 2015

Keywords

Discotic liquid crystals
synthesis
pyrazine

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10.1021/acs.orglett.5b01444

WK OL Revised FinalOther version, 284 KB

Andy Cammidge
- A.Cammidgeuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Professor of Chemistry
- Synthetic and Medicinal Chemistry - Member
Person: Research Group Member, Academic, Teaching and Research

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title = "A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge",

abstract = "Beta-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophe-none imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demon-strates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character",

keywords = "Discotic liquid crystals, synthesis, pyrazine",

author = "Weikang Xiao and Zhiqun He and {Remiro Buenamanana}, Sonia and Rebecca Turner and Min Xu and Xiao Yang and Xiping Jing and Cammidge, {Andrew N.}",

year = "2015",

doi = "10.1021/acs.orglett.5b01444",

language = "English",

volume = "17",

pages = "3286–3289",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge

AU - Xiao, Weikang

AU - He, Zhiqun

AU - Remiro Buenamanana, Sonia

AU - Turner, Rebecca

AU - Xu, Min

AU - Yang, Xiao

AU - Jing, Xiping

AU - Cammidge, Andrew N.

PY - 2015

Y1 - 2015

N2 - Beta-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophe-none imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demon-strates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character

AB - Beta-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophe-none imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demon-strates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character

KW - Discotic liquid crystals

KW - synthesis

KW - pyrazine

U2 - 10.1021/acs.orglett.5b01444

DO - 10.1021/acs.orglett.5b01444

M3 - Article

SN - 1523-7060

VL - 17

SP - 3286

EP - 3289

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge

Abstract

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Andy Cammidge

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