Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

5018106

Reference Type

Journal Article

Title

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

Author(s)

Sekine, K; Schulmeister, J; Paulus, F; Goetz, KP; Rominger, F; Rudolph, M; Zaumseil, J; Hashmi, ASK

Year

2019

Is Peer Reviewed?

Yes

Journal

Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765

Publisher

WILEY-V C H VERLAG GMBH

Location

WEINHEIM

Volume

Issue

Page Numbers

216-220

Language

English

PMID

30423210

DOI

10.1002/chem.201805637

Web of Science Id

WOS:000454705500026

URL

http://://WOS:000454705500026
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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.