Synthesis and morphology of asymmetric, alkyne-functionalised pentacene and 2-fluoroanthradithiophene

Craig M.S. Combe; David T. James; Jessica Wade; Andrew J.P. White; Ji Seon Kim; Iain Mcculloch

doi:10.1016/j.tetlet.2013.10.006

Synthesis and morphology of asymmetric, alkyne-functionalised pentacene and 2-fluoroanthradithiophene

Craig M.S. Combe^*, David T. James, Jessica Wade, Andrew J.P. White, Ji Seon Kim, Iain Mcculloch

^*Corresponding author for this work

Physical Sciences and Engineering

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

1 Scopus citations

Abstract

The performance of 6,13-(bis-triisopropylsilylethynyl)pentacene (TIPS-pentacene) and 1,1′-difluoro-5,11-(bis-triethylsilyl)acetylene-anthra[2,3-b:6,7-b′]dithiophene (TES-FADT) is highly dependent on the morphology enforced by their alkyl groups, with only triisopropylsilylethynyl and triethylsilylethynyl producing viable transistor devices, respectively. Asymmetric triisopropylsilylacetylene- and triethylsilylacetylene-functionalised pentacene and 2-fluoroanthradithiophene were synthesised to study the effects a small change to the solubilising groups has on the thin film morphology.

Original language	English (US)
Journal	Tetrahedron Letters
Volume	54
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.006
State	Published - Aug 17 2013

Keywords

Anthradithiophene
Crystallography
Morphology
Pentacene
Triethylsilylethynyl
Triisopropylsilylethynyl

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.10.006

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title = "Synthesis and morphology of asymmetric, alkyne-functionalised pentacene and 2-fluoroanthradithiophene",

abstract = "The performance of 6,13-(bis-triisopropylsilylethynyl)pentacene (TIPS-pentacene) and 1,1′-difluoro-5,11-(bis-triethylsilyl)acetylene-anthra[2,3-b:6,7-b′]dithiophene (TES-FADT) is highly dependent on the morphology enforced by their alkyl groups, with only triisopropylsilylethynyl and triethylsilylethynyl producing viable transistor devices, respectively. Asymmetric triisopropylsilylacetylene- and triethylsilylacetylene-functionalised pentacene and 2-fluoroanthradithiophene were synthesised to study the effects a small change to the solubilising groups has on the thin film morphology.",

keywords = "Anthradithiophene, Crystallography, Morphology, Pentacene, Triethylsilylethynyl, Triisopropylsilylethynyl",

author = "Combe, {Craig M.S.} and James, {David T.} and Jessica Wade and White, {Andrew J.P.} and Kim, {Ji Seon} and Iain Mcculloch",

year = "2013",

month = aug,

day = "17",

doi = "10.1016/j.tetlet.2013.10.006",

language = "English (US)",

volume = "54",

journal = "Tetrahedron Letters",

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publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis and morphology of asymmetric, alkyne-functionalised pentacene and 2-fluoroanthradithiophene

AU - Combe, Craig M.S.

AU - James, David T.

AU - Wade, Jessica

AU - White, Andrew J.P.

AU - Kim, Ji Seon

AU - Mcculloch, Iain

PY - 2013/8/17

Y1 - 2013/8/17

N2 - The performance of 6,13-(bis-triisopropylsilylethynyl)pentacene (TIPS-pentacene) and 1,1′-difluoro-5,11-(bis-triethylsilyl)acetylene-anthra[2,3-b:6,7-b′]dithiophene (TES-FADT) is highly dependent on the morphology enforced by their alkyl groups, with only triisopropylsilylethynyl and triethylsilylethynyl producing viable transistor devices, respectively. Asymmetric triisopropylsilylacetylene- and triethylsilylacetylene-functionalised pentacene and 2-fluoroanthradithiophene were synthesised to study the effects a small change to the solubilising groups has on the thin film morphology.

AB - The performance of 6,13-(bis-triisopropylsilylethynyl)pentacene (TIPS-pentacene) and 1,1′-difluoro-5,11-(bis-triethylsilyl)acetylene-anthra[2,3-b:6,7-b′]dithiophene (TES-FADT) is highly dependent on the morphology enforced by their alkyl groups, with only triisopropylsilylethynyl and triethylsilylethynyl producing viable transistor devices, respectively. Asymmetric triisopropylsilylacetylene- and triethylsilylacetylene-functionalised pentacene and 2-fluoroanthradithiophene were synthesised to study the effects a small change to the solubilising groups has on the thin film morphology.

KW - Anthradithiophene

KW - Crystallography

KW - Morphology

KW - Pentacene

KW - Triethylsilylethynyl

KW - Triisopropylsilylethynyl

UR - http://www.scopus.com/inward/record.url?scp=84942079325&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.10.006

DO - 10.1016/j.tetlet.2013.10.006

M3 - Article

VL - 54

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -

Synthesis and morphology of asymmetric, alkyne-functionalised pentacene and 2-fluoroanthradithiophene

Abstract

Keywords

ASJC Scopus subject areas

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