Fluorocarbon-modified organic semiconductors: Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties

Myung Han Yoon, Antonio Facchetti, Charlotte E. Stern, Tobin J Marks

Research output: Contribution to journalArticle

270 Citations (Scopus)

Abstract

We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5″-diphenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (1), 5,5′-bis-{1-[4-(thien-2-yl)phenyl]}-2, 2′-dithiophene (2), 4,4′-bis[5-(2,2′-dithiophenyl)]-biphenyl (3), 5,5″-diperfluorophenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (4), 5,5′-bis{1-[4-(thien-2-yl)perfluorophenyl]} -2,2′-dithiophene (5), 4,4′-bis[5-(2,2′-dithiophenyl)]- perfluorobiphenyl (6), 5,5″-diperfluorophenyl-2,2′:5′, 2″-tertthiophene (7), 5,5′-diperfluorophenyl-2,2′-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum film microstructural order is achieved. A very large n-channel mobility of ∼0.5 cm2/Vs with Ion/I off ratios > 108 is achieved for films of 4.

Original languageEnglish
Pages (from-to)5792-5801
Number of pages10
JournalJournal of the American Chemical Society
Volume128
Issue number17
DOIs
Publication statusPublished - May 3 2006

Fingerprint

Fluorocarbons
Thiophenes
Semiconductors
Semiconducting organic compounds
Thiophene
Oligomers
Electronic structure
Tuning
Crystal structure
Field effect transistors
Thin films
Molecular Structure
X-Ray Diffraction
Oxidation-Reduction
Growth temperature
Ions
Light absorption
Molecular structure
Temperature
Growth

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Fluorocarbon-modified organic semiconductors : Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties. / Yoon, Myung Han; Facchetti, Antonio; Stern, Charlotte E.; Marks, Tobin J.

In: Journal of the American Chemical Society, Vol. 128, No. 17, 03.05.2006, p. 5792-5801.

Research output: Contribution to journalArticle

@article{a63051861fd84805bf1cebcca3b2b3e9,
title = "Fluorocarbon-modified organic semiconductors: Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties",
abstract = "We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5″-diphenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (1), 5,5′-bis-{1-[4-(thien-2-yl)phenyl]}-2, 2′-dithiophene (2), 4,4′-bis[5-(2,2′-dithiophenyl)]-biphenyl (3), 5,5″-diperfluorophenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (4), 5,5′-bis{1-[4-(thien-2-yl)perfluorophenyl]} -2,2′-dithiophene (5), 4,4′-bis[5-(2,2′-dithiophenyl)]- perfluorobiphenyl (6), 5,5″-diperfluorophenyl-2,2′:5′, 2″-tertthiophene (7), 5,5′-diperfluorophenyl-2,2′-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum film microstructural order is achieved. A very large n-channel mobility of ∼0.5 cm2/Vs with Ion/I off ratios > 108 is achieved for films of 4.",
author = "Yoon, {Myung Han} and Antonio Facchetti and Stern, {Charlotte E.} and Marks, {Tobin J}",
year = "2006",
month = "5",
day = "3",
doi = "10.1021/ja060016a",
language = "English",
volume = "128",
pages = "5792--5801",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Fluorocarbon-modified organic semiconductors

T2 - Molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties

AU - Yoon, Myung Han

AU - Facchetti, Antonio

AU - Stern, Charlotte E.

AU - Marks, Tobin J

PY - 2006/5/3

Y1 - 2006/5/3

N2 - We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5″-diphenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (1), 5,5′-bis-{1-[4-(thien-2-yl)phenyl]}-2, 2′-dithiophene (2), 4,4′-bis[5-(2,2′-dithiophenyl)]-biphenyl (3), 5,5″-diperfluorophenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (4), 5,5′-bis{1-[4-(thien-2-yl)perfluorophenyl]} -2,2′-dithiophene (5), 4,4′-bis[5-(2,2′-dithiophenyl)]- perfluorobiphenyl (6), 5,5″-diperfluorophenyl-2,2′:5′, 2″-tertthiophene (7), 5,5′-diperfluorophenyl-2,2′-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum film microstructural order is achieved. A very large n-channel mobility of ∼0.5 cm2/Vs with Ion/I off ratios > 108 is achieved for films of 4.

AB - We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5″-diphenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (1), 5,5′-bis-{1-[4-(thien-2-yl)phenyl]}-2, 2′-dithiophene (2), 4,4′-bis[5-(2,2′-dithiophenyl)]-biphenyl (3), 5,5″-diperfluorophenyl-2,2′:5′,2″:5″, 2‴-quaterthiophene (4), 5,5′-bis{1-[4-(thien-2-yl)perfluorophenyl]} -2,2′-dithiophene (5), 4,4′-bis[5-(2,2′-dithiophenyl)]- perfluorobiphenyl (6), 5,5″-diperfluorophenyl-2,2′:5′, 2″-tertthiophene (7), 5,5′-diperfluorophenyl-2,2′-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum film microstructural order is achieved. A very large n-channel mobility of ∼0.5 cm2/Vs with Ion/I off ratios > 108 is achieved for films of 4.

UR - http://www.scopus.com/inward/record.url?scp=33646540412&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646540412&partnerID=8YFLogxK

U2 - 10.1021/ja060016a

DO - 10.1021/ja060016a

M3 - Article

C2 - 16637648

AN - SCOPUS:33646540412

VL - 128

SP - 5792

EP - 5801

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 17

ER -