On‐surface synthesis of ethynylene bridged-anthracene polymers

0509954 - FZÚ 2020 RIV DE eng J - Journal Article
Sánchez-Grande, A. - De La Torre Cerdeño, Bruno - Santos, J. - Cirera, B. - Lauwaet, K. - Chutora, T. - Edalatmanesh, S. - Mutombo, Pingo - Rosen, J. - Zbořil, R. - Miranda, R. - Bjork, J. - Jelínek, Pavel - Martín, N. - Ecija, D.
On‐surface synthesis of ethynylene bridged-anthracene polymers.
Angewandte Chemie - International Edition. Roč. 58, č. 50 (2019), s. 6559-6563. ISSN 1433-7851. E-ISSN 1521-3773
R&D Projects: GA MŠMT LM2015087
Grant - others:AV ČR(CZ) Praemium Academiae
Institutional support: RVO:68378271
Keywords : nc-AFM * on surface chemistry * polymers
OECD category: Physical chemistry
Impact factor: 12.959, year: 2019
Method of publishing: Open access

Here, we report an unprecedented on‐surface synthesis protocol to overcome such difficulties, being able to design poly(p‐anthracene ethynylene) molecular wires on an Au(111) surface. To this aim, a quinoid anthracene precursor endowed with =CBr2 moieties is deposited and annealed to 400 K resulting in anthracene‐based polymers, with a measured electronic bandgap of 1.5 eV. High‐resolution non‐contact atomic force microscopy with a CO functionalized tip unambiguously corroborates the nature of the ethynylene bridge bond between anthracene moieties. Complementary theoretical simulations of the reaction pathways illustrate the mechanism of the chemical reaction, highlighting three major steps: dehalogenation, diffusion of surface‐stabilized carbenes, and homocoupling enabling the formation of an ethynylene bridge.
Permanent Link: http://hdl.handle.net/11104/0300539