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Synfacts 2015; 11(1): 0036
DOI: 10.1055/s-0034-1379666
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Diels–Alder Approach to Graphene Nanoribbon Precursors

Contributor(s):
Timothy M. Swager
,
Kathleen R. White
Feng X, * Müllen K. * et al. Max Planck Institute for Polymer Research, Mainz and Free University Berlin, Germany; University of Leuven, Belgium; FOM Institute AMOLF, Amsterdam, The Netherlands; Aarhus University, Denmark; Manchester University, UK
Bottom-Up Synthesis of Liquid-Phase-Processable Graphene Nanoribbons with Near-Infrared Absorption.

ACS Nano 2014;
8: 11622-11630
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

graphene nanoribbons - cyclodehydro-genation - Diels–Alder reaction - near-infrared absorption

Significance

Bottom-up approaches to graphene nanoribbons (GNRs) have been limited by the short length of nanoribbons produced (<50 nm) or the requirement for metal surfaces. The authors report a bottom-up approach to the synthesis of longer (>100 nm), structurally defined GNRs using an AB-type Diels–Alder polymerization to form nanoribbon precursors 8 that can be planarized to GNRs 9 by oxidative cyclodehydrogenation with FeCl3.


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Comment

Despite the formation of multiple regioisomers after the Diels–Alder polymerization of asymmetrical monomer 7, upon planarization, all isomers of 8 yielded an identical GNR structure (9). Polymerization of 7 was carried out both in solution and melt, with melt yielding GNR precursors of significantly higher M w (230,000–550,000 g/mol versus 42,000–78,000 g/mol for solution polymerization).


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