Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

Barnaby T. Haire; Kane W. J. Heard; Mark S. Little; Adam V. S. Parry; James Raftery; Peter Quayle; Stephen G. Yeates

doi:10.1002/chem.201501861

Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

Barnaby T. Haire, Kane W. J. Heard, Mark S. Little, Adam V. S. Parry, James Raftery, Peter Quayle, Stephen G. Yeates

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Abstract

A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one- or two-directional benzannulation reactions of readily available (ortho-allylaryl)trichloroacetates (the “BHQ” reaction). Palladium-catalysed cross-coupling reactions of the so-formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials.

Original language	English
Pages (from-to)	9970-9974
Number of pages	4
Journal	Chemistry: A European Journal
Volume	21
Issue number	28
DOIs	https://doi.org/10.1002/chem.201501861
Publication status	Published - 8 Jun 2015

Keywords

benzannulation
coupling
cyclization
polycyclic aromatic hydrocarbons
polycycles

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10.1002/chem.201501861

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CCDC 1040410: Experimental Crystal Structure Determination
Haire, B. (Contributor), Heard, K. (Contributor), Little, M. (Contributor), Parry, A. (Contributor), Raftery, J. (Contributor), Quayle, P. (Contributor) & Yeates, S. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/cc13xmm8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13xmm8&sid=DataCite
Dataset
CCDC 1040411: Experimental Crystal Structure Determination
Haire, B. (Contributor), Heard, K. (Contributor), Little, M. (Contributor), Parry, A. (Contributor), Raftery, J. (Contributor), Quayle, P. (Contributor) & Yeates, S. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/cc13xmn9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13xmn9&sid=DataCite
Dataset
CCDC 1040540: Experimental Crystal Structure Determination
Haire, B. (Contributor), Heard, K. (Contributor), Little, M. (Contributor), Parry, A. (Contributor), Raftery, J. (Contributor), Quayle, P. (Contributor) & Yeates, S. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/cc13xrtl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13xrtl&sid=DataCite
Dataset

Cite this

@article{f448173bc5144729a85d3f8832b9cdea,

title = "Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties",

abstract = "A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one- or two-directional benzannulation reactions of readily available (ortho-allylaryl)trichloroacetates (the “BHQ” reaction). Palladium-catalysed cross-coupling reactions of the so-formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials.",

keywords = "benzannulation, coupling, cyclization, polycyclic aromatic hydrocarbons, polycycles",

author = "Haire, {Barnaby T.} and Heard, {Kane W. J.} and Little, {Mark S.} and Parry, {Adam V. S.} and James Raftery and Peter Quayle and Yeates, {Stephen G.}",

year = "2015",

month = jun,

day = "8",

doi = "10.1002/chem.201501861",

language = "English",

volume = "21",

pages = "9970--9974",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons Ltd",

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TY - JOUR

T1 - Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

AU - Haire, Barnaby T.

AU - Heard, Kane W. J.

AU - Little, Mark S.

AU - Parry, Adam V. S.

AU - Raftery, James

AU - Quayle, Peter

AU - Yeates, Stephen G.

PY - 2015/6/8

Y1 - 2015/6/8

N2 - A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one- or two-directional benzannulation reactions of readily available (ortho-allylaryl)trichloroacetates (the “BHQ” reaction). Palladium-catalysed cross-coupling reactions of the so-formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials.

AB - A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one- or two-directional benzannulation reactions of readily available (ortho-allylaryl)trichloroacetates (the “BHQ” reaction). Palladium-catalysed cross-coupling reactions of the so-formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials.

KW - benzannulation

KW - coupling

KW - cyclization

KW - polycyclic aromatic hydrocarbons

KW - polycycles

U2 - 10.1002/chem.201501861

DO - 10.1002/chem.201501861

M3 - Article

SN - 0947-6539

VL - 21

SP - 9970

EP - 9974

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 28

ER -

Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

Abstract

Keywords

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Datasets

CCDC 1040410: Experimental Crystal Structure Determination

CCDC 1040411: Experimental Crystal Structure Determination

CCDC 1040540: Experimental Crystal Structure Determination

Cite this