Synthesis and characterization of diperfluorooctyl-substituted phenylene-thiophene oligomers as n-type semiconductors. Molecular structure-film microstructure-mobility relationships, organic field-effect transistors, and transistor nonvolatile memory elements

Antonio Facchetti, Joseph Letizia, Myung Han Yoon, Melissa Mushrush, Howard E. Katz, Tobin J Marks

Research output: Contribution to journalArticle

146 Citations (Scopus)

Abstract

A new series of mixed phenylene-thiophene oligomers with terminal n-perfluorooctyl groups has been synthesized. These compounds are 2,5-bis(4-n-perfluorooctylphenyl)-thiophene (DFO-PTP, 1), 5,5′-bis(4-n- perfluorooctylphenyl)-2,2′-bithiophene (DFO-PTTP, 2), 5,5″-bis(4-n- perfluorooctylphenyl)-2,2′:5′,2″-terthiophene (DFO-PT 3P, 3), 5,5‴-bis(4-n-perfluorooctylphenyl)-2,2′: 5′,2″:5″,2‴-quaterthiophene (DFO-PT4P, 4), and 1,4-bis[5-(4-n-perfluorooctylphenyl)-2-thienyl]benzene (DH-PTPTP, 5). These systems have been characterized by 1H and 19F NMR, elemental analysis or HRMS, optical absorption and emission spectroscopies, differential scanning calorimetry, and thermogravimetric analysis. Vacuum-deposited films were characterized by optical absorption and emission spectroscopy, X-ray diffraction, scanning electron microscopy, and field effect transistor measurements. As thin films, all of the fluorinated compounds are n-type semiconductors with carrier mobilities ranging from ∼ 10-6 to ∼ 0.1 cm2 V-1 s-1, depending on the substrate deposition temperature. Furthermore, these films exhibit very large current Ion:Ioff ratios (up to ∼ 107) due to substantially suppressed off-currents. Particularly interesting is straightforwardly synthesized DFO-PTTP (2), which displays a combination of high mobility, high current Ion:Ioff ratio, and reversible, tunable, and stable memory effects.

Original languageEnglish
Pages (from-to)4715-4727
Number of pages13
JournalChemistry of Materials
Volume16
Issue number23
DOIs
Publication statusPublished - Nov 16 2004

Fingerprint

Organic field effect transistors
Thiophenes
Emission spectroscopy
Thiophene
Absorption spectroscopy
Oligomers
Light absorption
Molecular structure
Transistors
Ions
Semiconductor materials
Data storage equipment
Microstructure
Carrier mobility
Field effect transistors
Benzene
Thermogravimetric analysis
Differential scanning calorimetry
Nuclear magnetic resonance
Vacuum

ASJC Scopus subject areas

  • Materials Chemistry
  • Materials Science(all)

Cite this

@article{e903da48c1e2485bb2041f6eacea07fa,
title = "Synthesis and characterization of diperfluorooctyl-substituted phenylene-thiophene oligomers as n-type semiconductors. Molecular structure-film microstructure-mobility relationships, organic field-effect transistors, and transistor nonvolatile memory elements",
abstract = "A new series of mixed phenylene-thiophene oligomers with terminal n-perfluorooctyl groups has been synthesized. These compounds are 2,5-bis(4-n-perfluorooctylphenyl)-thiophene (DFO-PTP, 1), 5,5′-bis(4-n- perfluorooctylphenyl)-2,2′-bithiophene (DFO-PTTP, 2), 5,5″-bis(4-n- perfluorooctylphenyl)-2,2′:5′,2″-terthiophene (DFO-PT 3P, 3), 5,5‴-bis(4-n-perfluorooctylphenyl)-2,2′: 5′,2″:5″,2‴-quaterthiophene (DFO-PT4P, 4), and 1,4-bis[5-(4-n-perfluorooctylphenyl)-2-thienyl]benzene (DH-PTPTP, 5). These systems have been characterized by 1H and 19F NMR, elemental analysis or HRMS, optical absorption and emission spectroscopies, differential scanning calorimetry, and thermogravimetric analysis. Vacuum-deposited films were characterized by optical absorption and emission spectroscopy, X-ray diffraction, scanning electron microscopy, and field effect transistor measurements. As thin films, all of the fluorinated compounds are n-type semiconductors with carrier mobilities ranging from ∼ 10-6 to ∼ 0.1 cm2 V-1 s-1, depending on the substrate deposition temperature. Furthermore, these films exhibit very large current Ion:Ioff ratios (up to ∼ 107) due to substantially suppressed off-currents. Particularly interesting is straightforwardly synthesized DFO-PTTP (2), which displays a combination of high mobility, high current Ion:Ioff ratio, and reversible, tunable, and stable memory effects.",
author = "Antonio Facchetti and Joseph Letizia and Yoon, {Myung Han} and Melissa Mushrush and Katz, {Howard E.} and Marks, {Tobin J}",
year = "2004",
month = "11",
day = "16",
doi = "10.1021/cm0495008",
language = "English",
volume = "16",
pages = "4715--4727",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

T1 - Synthesis and characterization of diperfluorooctyl-substituted phenylene-thiophene oligomers as n-type semiconductors. Molecular structure-film microstructure-mobility relationships, organic field-effect transistors, and transistor nonvolatile memory elements

AU - Facchetti, Antonio

AU - Letizia, Joseph

AU - Yoon, Myung Han

AU - Mushrush, Melissa

AU - Katz, Howard E.

AU - Marks, Tobin J

PY - 2004/11/16

Y1 - 2004/11/16

N2 - A new series of mixed phenylene-thiophene oligomers with terminal n-perfluorooctyl groups has been synthesized. These compounds are 2,5-bis(4-n-perfluorooctylphenyl)-thiophene (DFO-PTP, 1), 5,5′-bis(4-n- perfluorooctylphenyl)-2,2′-bithiophene (DFO-PTTP, 2), 5,5″-bis(4-n- perfluorooctylphenyl)-2,2′:5′,2″-terthiophene (DFO-PT 3P, 3), 5,5‴-bis(4-n-perfluorooctylphenyl)-2,2′: 5′,2″:5″,2‴-quaterthiophene (DFO-PT4P, 4), and 1,4-bis[5-(4-n-perfluorooctylphenyl)-2-thienyl]benzene (DH-PTPTP, 5). These systems have been characterized by 1H and 19F NMR, elemental analysis or HRMS, optical absorption and emission spectroscopies, differential scanning calorimetry, and thermogravimetric analysis. Vacuum-deposited films were characterized by optical absorption and emission spectroscopy, X-ray diffraction, scanning electron microscopy, and field effect transistor measurements. As thin films, all of the fluorinated compounds are n-type semiconductors with carrier mobilities ranging from ∼ 10-6 to ∼ 0.1 cm2 V-1 s-1, depending on the substrate deposition temperature. Furthermore, these films exhibit very large current Ion:Ioff ratios (up to ∼ 107) due to substantially suppressed off-currents. Particularly interesting is straightforwardly synthesized DFO-PTTP (2), which displays a combination of high mobility, high current Ion:Ioff ratio, and reversible, tunable, and stable memory effects.

AB - A new series of mixed phenylene-thiophene oligomers with terminal n-perfluorooctyl groups has been synthesized. These compounds are 2,5-bis(4-n-perfluorooctylphenyl)-thiophene (DFO-PTP, 1), 5,5′-bis(4-n- perfluorooctylphenyl)-2,2′-bithiophene (DFO-PTTP, 2), 5,5″-bis(4-n- perfluorooctylphenyl)-2,2′:5′,2″-terthiophene (DFO-PT 3P, 3), 5,5‴-bis(4-n-perfluorooctylphenyl)-2,2′: 5′,2″:5″,2‴-quaterthiophene (DFO-PT4P, 4), and 1,4-bis[5-(4-n-perfluorooctylphenyl)-2-thienyl]benzene (DH-PTPTP, 5). These systems have been characterized by 1H and 19F NMR, elemental analysis or HRMS, optical absorption and emission spectroscopies, differential scanning calorimetry, and thermogravimetric analysis. Vacuum-deposited films were characterized by optical absorption and emission spectroscopy, X-ray diffraction, scanning electron microscopy, and field effect transistor measurements. As thin films, all of the fluorinated compounds are n-type semiconductors with carrier mobilities ranging from ∼ 10-6 to ∼ 0.1 cm2 V-1 s-1, depending on the substrate deposition temperature. Furthermore, these films exhibit very large current Ion:Ioff ratios (up to ∼ 107) due to substantially suppressed off-currents. Particularly interesting is straightforwardly synthesized DFO-PTTP (2), which displays a combination of high mobility, high current Ion:Ioff ratio, and reversible, tunable, and stable memory effects.

UR - http://www.scopus.com/inward/record.url?scp=8444249278&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=8444249278&partnerID=8YFLogxK

U2 - 10.1021/cm0495008

DO - 10.1021/cm0495008

M3 - Article

VL - 16

SP - 4715

EP - 4727

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 23

ER -