Naphtho[2,3- b: 6,7- b']dichalcogenophenes: Syntheses, characterizations, and chalcogene atom effects on organic field-effect transistor and organic photovoltaic devices

Masahiro Nakano, Hiroki Mori, Shoji Shinamura, Kazuo Takimiya

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C 60 or C 70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO 2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm 2 V -1 s -1 and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.

Original languageEnglish
Pages (from-to)190-198
Number of pages9
JournalChemistry of Materials
Volume24
Issue number1
DOIs
Publication statusPublished - Jan 10 2012
Externally publishedYes

Fingerprint

Organic field effect transistors
Atoms
Semiconducting organic compounds
Nondestructive examination
Electronic structure
Thin film devices
Vacuum deposition
Thin films
Molecular orientation
Conversion efficiency
Crystalline materials
Derivatives
Substrates

Keywords

  • electronic structure
  • naphthodichalcogenophene
  • organic field-effect transistor
  • organic photovoltaic
  • organic semiconductor

ASJC Scopus subject areas

  • Materials Chemistry
  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Naphtho[2,3- b : 6,7- b']dichalcogenophenes: Syntheses, characterizations, and chalcogene atom effects on organic field-effect transistor and organic photovoltaic devices. / Nakano, Masahiro; Mori, Hiroki; Shinamura, Shoji; Takimiya, Kazuo.

In: Chemistry of Materials, Vol. 24, No. 1, 10.01.2012, p. 190-198.

Research output: Contribution to journalArticle

@article{0c1aa6f5aa6845da896c86282f93227c,
title = "Naphtho[2,3- b: 6,7- b']dichalcogenophenes: Syntheses, characterizations, and chalcogene atom effects on organic field-effect transistor and organic photovoltaic devices",
abstract = "New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C 60 or C 70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO 2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm 2 V -1 s -1 and as a donor layer in OPVs with power conversion efficiencies of up to 2.0{\%}, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.",
keywords = "electronic structure, naphthodichalcogenophene, organic field-effect transistor, organic photovoltaic, organic semiconductor",
author = "Masahiro Nakano and Hiroki Mori and Shoji Shinamura and Kazuo Takimiya",
year = "2012",
month = "1",
day = "10",
doi = "10.1021/cm202853b",
language = "English",
volume = "24",
pages = "190--198",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Naphtho[2,3- b

T2 - 6,7- b']dichalcogenophenes: Syntheses, characterizations, and chalcogene atom effects on organic field-effect transistor and organic photovoltaic devices

AU - Nakano, Masahiro

AU - Mori, Hiroki

AU - Shinamura, Shoji

AU - Takimiya, Kazuo

PY - 2012/1/10

Y1 - 2012/1/10

N2 - New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C 60 or C 70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO 2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm 2 V -1 s -1 and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.

AB - New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C 60 or C 70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO 2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm 2 V -1 s -1 and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.

KW - electronic structure

KW - naphthodichalcogenophene

KW - organic field-effect transistor

KW - organic photovoltaic

KW - organic semiconductor

UR - http://www.scopus.com/inward/record.url?scp=84855701710&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84855701710&partnerID=8YFLogxK

U2 - 10.1021/cm202853b

DO - 10.1021/cm202853b

M3 - Article

AN - SCOPUS:84855701710

VL - 24

SP - 190

EP - 198

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 1

ER -