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CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 001-018
DOI: 10.1055/s-0039-1700846
Review
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2019) The Author(s).

Starphenes and Phenes: Structures and Properties

Elias C. Rüdiger
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, FRG, Email: freudenberg@oci.uni-heidelberg.de   Email: uwe.bunz@oci.uni-heidelberg.de
,
Matthias Müller
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, FRG, Email: freudenberg@oci.uni-heidelberg.de   Email: uwe.bunz@oci.uni-heidelberg.de
,
Jan Freudenberg
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, FRG, Email: freudenberg@oci.uni-heidelberg.de   Email: uwe.bunz@oci.uni-heidelberg.de
b   InnovationLab, Speyerer Straße 4, 69115 Heidelberg, Germany
,
Uwe H. F. Bunz 
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, FRG, Email: freudenberg@oci.uni-heidelberg.de   Email: uwe.bunz@oci.uni-heidelberg.de
c   Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120 Heidelberg, FRG
› Author Affiliations Funding Information: We thank the DFG (SFB 1249) for generous financial support. Matthias Müller thanks the Fonds der Chemischen Industrie for a PhD scholarship.
Further Information

Publication History

Received: 10 April 2019

Accepted after revision: 19 June 2019

Publication Date:
25 November 2019 (online)

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Abstract

Acenes have been known for a long time but their larger congeners, starphenes and phenes, have only been recently accessible as processable and characterizable derivatives. In this personalized review, we delineate the synthetic approach developed by our group over the last four years. Nickel-mediated Yamamoto coupling of ortho-dibromoacenes generates cyclotrimers. If performed in a shotgun approach, i.e. with substituted 2,3-dibromotetracene or -pentacene in the presence of ortho-dibromobenzene or ortho-dibromoveratrole, trimeric phenes and tetramers would result. Cyclotrimers formed by a pentacenylene and two phenylenes are formally dibenzo[a,c]hexacenes. A direct way to obtain these species is to employ Stille coupling of a dimethylstannafluorene with 2,3-dibromoacenes. If tetrabromoanthracenes or tetrabromopentacenes are fed into this process, tetrabenzopentacene and tetrabenzoheptacenes are easily accessible. Optical and quantum-chemical characterizations provide insight into the electronic situation and aromaticity of these species.

Key words

acenes - phenes - starphenes
 

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