Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence

Urrego-Riveros, Sara; Bremer, Matthias; Hoffmann, Jonas; Heitmann, Anne Sofie Busk; Reynaldo, Thibault; Buhl, Janek; Gates, Paul J.; Sönnichsen, Frank D.; Hissler, Muriel; Gerken, Martina; Staubitz, Anne

doi:10.1039/c9qo00947g

Cited by 1 publication

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“…Herein, we developed a hexatopic monomer by the three-fold attachment of a ditopic moiety 2,6-dimethylpyridine to a phenyl ring at its meta -positions (Scheme a), − which can be used for the construction of two-dimensional vinylene-linked COFs with heteroporous structures. Their topology-directed semiconducting behaviors related to the partly interrupted π-electron delocalization and photocatalytic activities for the chemoselective bromination of aromatic compounds were explored (Scheme c).…”

Section: Introductionmentioning

confidence: 99%

Hexatopic Vertex-Directed Approach to Vinylene-Linked Covalent Organic Frameworks with Heteroporous Topologies

Meng

et al. 2023

J. Am. Chem. Soc.

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A D 3h -symmetric hexatopic monomer was first prepared by attaching the three-fold ditopic moiety 2,6dimethylpyridine to the meta-positions of a phenyl ring. It was further condensed at its six pyridylmethyl carbons with linear ditopic aromatic dialdehydes, resulting in two vinylene-linked COFs with heteroporous topologies, as revealed by powder X-ray diffraction (PXRD), nitrogen sorption, and pore-size distribution analyses, as well as transmission electron microscopy (TEM) image. The linear-and cross-conjugations, respectively, arising from the 2,6-linked pyridines and meta-linked phenylenes in the hexatopic nodes rendered the resultant COFs with well-patterned π-delocalization, allowing for efficiently catalyzing the bromination of aromatic derivatives with the pore-size-dependent conversion yields and regioselectivity under the irradiation of green light.

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Section: Introductionmentioning

confidence: 99%

Hexatopic Vertex-Directed Approach to Vinylene-Linked Covalent Organic Frameworks with Heteroporous Topologies

Meng

et al. 2023

J. Am. Chem. Soc.

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Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence

Abstract: A synthetic strategy for push–pull oligomers is based on a nucleophile and electrophile selective synthesis of the corresponding monomers.

Cited by 1 publication

References 45 publications

Hexatopic Vertex-Directed Approach to Vinylene-Linked Covalent Organic Frameworks with Heteroporous Topologies

Hexatopic Vertex-Directed Approach to Vinylene-Linked Covalent Organic Frameworks with Heteroporous Topologies

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