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

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

3 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)
Pages (from-to)	6814-6818
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.006
State	Published - Dec 11 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Anthradithiophene
Crystallography
Morphology
Pentacene
Triethylsilylethynyl
Triisopropylsilylethynyl

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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{\textquoteright}-difluoro-5,11-(bis-triethylsilyl)acetylene-anthra[2,3-b:6,7-b{\textquoteright}]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",

note = "Publisher Copyright: {\textcopyright} 2013",

year = "2013",

month = dec,

day = "11",

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

language = "English (US)",

volume = "54",

pages = "6814--6818",

journal = "Tetrahedron Letters",

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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 - 2013/12/11

Y1 - 2013/12/11

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 - https://www.scopus.com/pages/publications/85063947049

UR - https://www.scopus.com/pages/publications/85063947049#tab=citedBy

U2 - 10.1016/j.tetlet.2013.10.006

DO - 10.1016/j.tetlet.2013.10.006

M3 - Article

AN - SCOPUS:85063947049

SN - 0040-4039

VL - 54

SP - 6814

EP - 6818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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