2026-06-29T07:40:55Zhttps://docta.ucm.es/rest/oai/requestoai:docta.ucm.es:20.500.14352/138682023-07-18T01:58:24Zcom_20.500.14352_14col_20.500.14352_15
On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers
Sánchez Grande, Ana
De la Torre, Bruno
Santos, José
Cirera, Borja
Lauwaet, Koen
Chutora, Taras
Edalatmanesh, Shayan
Rosen, Johanna
Zboril, Radek
Miranda, Rodolfo
Björk, Jonas
Jelínek, Pavel
Martín, Nazario
Ecija, David
547
Acenes
low-band-gap semiconductors
polymers
scanning probe microscopy
surface chemistry
Química orgánica (Química)
2306 Química Orgánica
Engineering low-band-gap p-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 =CBr2 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 p-conjugated polymers based on oligoacene precursors and pave new avenues for advancing the emerging field of on-surface synthesis.
Unión Europea. H2020
Unión Europea. FP7
Ministerio de Economía y Competitividad (MINECO)
Comunidad de Madrid
Programa Ramón y Cajal Programa
Centro de Excelencia Severo Ochoa
Praemium Academie of the Academy of Science of the Czech Republic
European Structural and Investment Funds and the Czech Ministry of Education, Youth, and Sports
Czech Science Foundation
Swedish Research Council
Swedish Strategic Research Area in Materials Science on Functional Materials at Linkçping University
Depto. de Química Orgánica
Fac. de Ciencias Químicas
TRUE
pub
2023-06-17T13:37:16Z
2023-06-17T13:37:16Z
2019-05
journal article
https://hdl.handle.net/20.500.14352/13868
1433-7851
10.1002/anie.201814154
eng
CHIRALLCARBON (320441); ELECNANO (766555)
AMAROUT-II (291803)
(FIS 2013-40667-P; FIS 2015-67287-P, CTQ201783531-R, and CTQ2016-81911-REDT)
QUIMTRONIC (Y2018/NMT-4783); MAD2D (S2013/ MIT-3007) ; NANOMAGCOST-CM (S2018/NMT-4321) ; PHOTOCARBON (S2013/MIT-2841)
(RYC-2012-11133)
(SEV-2016-0686)
MEYS LM2015087 and GACR 18–09914S
(Project No. CZ.02.1.01/0.0/0.0/16 019/0000754)
Project No. 19-27454X
(642-2013-2080)
(Faculty Grant SFO-Mat-LiU No 2009 00971)
open access
application/pdf
Wiley-VCH