Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors

Kohei Sekine, Jürgen Schulmeister, Fabian Paulus, Katelyn P. Goetz, Frank Rominger, Matthias Rudolph, Jana Zaumseil, A. Stephen K. Hashmi

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.

Original languageEnglish
Pages (from-to)216-220
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 2 2019

Fingerprint

Semiconducting organic compounds
Naphthalene
Benzene
Gold
Transistors
Naphthalenes
Crystal structure
Hole mobility
Isomers
Optoelectronic devices
Ligands
Substrates
naphthalene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors. / Sekine, Kohei; Schulmeister, Jürgen; Paulus, Fabian; Goetz, Katelyn P.; Rominger, Frank; Rudolph, Matthias; Zaumseil, Jana; Hashmi, A. Stephen K.

In: Chemistry - A European Journal, Vol. 25, No. 1, 02.01.2019, p. 216-220.

Research output: Contribution to journalArticle

Sekine, Kohei ; Schulmeister, Jürgen ; Paulus, Fabian ; Goetz, Katelyn P. ; Rominger, Frank ; Rudolph, Matthias ; Zaumseil, Jana ; Hashmi, A. Stephen K. / Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 1. pp. 216-220.
@article{ca3b708c722b4a2e800bbd50ce4a864b,
title = "Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors",
abstract = "The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.",
author = "Kohei Sekine and J{\"u}rgen Schulmeister and Fabian Paulus and Goetz, {Katelyn P.} and Frank Rominger and Matthias Rudolph and Jana Zaumseil and Hashmi, {A. Stephen K.}",
year = "2019",
month = "1",
day = "2",
doi = "10.1002/chem.201805637",
language = "English",
volume = "25",
pages = "216--220",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "1",

}

TY - JOUR

T1 - Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors

AU - Sekine, Kohei

AU - Schulmeister, Jürgen

AU - Paulus, Fabian

AU - Goetz, Katelyn P.

AU - Rominger, Frank

AU - Rudolph, Matthias

AU - Zaumseil, Jana

AU - Hashmi, A. Stephen K.

PY - 2019/1/2

Y1 - 2019/1/2

N2 - The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.

AB - The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.

UR - http://www.scopus.com/inward/record.url?scp=85058838651&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85058838651&partnerID=8YFLogxK

U2 - 10.1002/chem.201805637

DO - 10.1002/chem.201805637

M3 - Article

C2 - 30423210

AN - SCOPUS:85058838651

VL - 25

SP - 216

EP - 220

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 1

ER -