Anthracene-Porphyrin Nanoribbons

0573625 - ÚOCHB 2024 RIV US eng J - Journal Article
Zhu, H. - Chen, Q. - Rončević, Igor - Christensen, K. E. - Anderson, H. L.
Anthracene-Porphyrin Nanoribbons.
Angewandte Chemie - International Edition. Roč. 62, č. 31 (2023), č. článku e202307035. ISSN 1433-7851. E-ISSN 1521-3773
Research Infrastructure: e-INFRA CZ - 90140
Institutional support: RVO:61388963
Keywords : graphene nanoribbons * metal exchange * NIR absorption * nanostructures * porphyrinoids
OECD category: Organic chemistry
Impact factor: 16.6, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/anie.202307035

π-Conjugated nanoribbons attract interest because of their unusual electronic structures and charge-transport behavior. Here, we report the synthesis of a series of fully edge-fused porphyrin-anthracene oligomeric ribbons (dimer and trimer), together with a computational study of the corresponding infinite polymer. The porphyrin dimer and trimer were synthesized in high yield, via oxidative cyclodehydrogenation of singly linked precursors, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoromethanesulfonic acid (TfOH). The crystal structure of the dimer shows that the central π-system is flat, with a slight S-shaped wave distortion at each porphyrin terminal. The extended π-conjugation causes a dramatic red-shift in the absorption spectra: the absorption maxima of the fused dimer and trimer appear at 1188 nm and 1642 nm, respectively (for the nickel complexes dissolved in toluene). The coordinated metal in the dimer was changed from Ni to Mg, using p-tolylmagnesium bromide, providing access to free-base and Zn complexes. These results open a versatile avenue to longer π-conjugated nanoribbons with integrated metalloporphyrin units.
Permanent Link: https://hdl.handle.net/11104/0344027