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On‐Surface Synthesis of Ethynylene‐Bridged Anthracene Polymers
Author(s) -
SánchezGrande Ana,
de la Torre Bruno,
Santos José,
Cirera Borja,
Lauwaet Koen,
Chutora Taras,
Edalatmanesh Shayan,
Mutombo Pingo,
Rosen Johanna,
Zbořil Radek,
Miranda Rodolfo,
Björk Jonas,
Jelínek Pavel,
Martín Nazario,
Écija David
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201814154
Subject(s) - anthracene , conjugated system , polymer , halogenation , solubility , materials science , nanotechnology , surface modification , combinatorial chemistry , chemistry , polymer chemistry , organic chemistry
Abstract Engineering low‐band‐gap π‐conjugated polymers is a growing area in basic and applied research. The main synthetic challenge lies in the solubility of the starting materials, which precludes advancements in the field. Here, we report an on‐surface synthesis protocol to overcome such difficulties and produce poly( p ‐anthracene ethynylene) molecular wires on Au(111). To this aim, a quinoid anthracene precursor with =CBr 2 moieties is deposited and annealed to 400 K, resulting in anthracene‐based polymers. High‐resolution nc‐AFM measurements confirm the nature of the ethynylene‐bridge bond between the anthracene moieties. Theoretical simulations illustrate the mechanism of the chemical reaction, highlighting three major steps: dehalogenation, diffusion of surface‐stabilized carbenes, and homocoupling, which enables the formation of an ethynylene bridge. Our results introduce a novel chemical protocol to design π‐conjugated polymers based on oligoacene precursors and pave new avenues for advancing the emerging field of on‐surface synthesis.