Beilstein Arch. 2025, 202523. https://doi.org/10.3762/bxiv.2025.23.v1
Published 15 Apr 2025
Development of three-dimensional (3D) building blocks is a key to change tight molecular assemblies of rigid π-conjugated planes into organic functional materials endowed with molecular-size cavities. To increase the diversity of available 3D building blocks, we herein report electrophilic formylation of naphthalene-fused [3.3.3]- and [4.3.3]propellanes as the first selective single-point functionalization by virtue of through-space electronic communications between the naphthalene units. The propellane skeletons have well-defined 3D structures and moderate flexibility at the same time. Therefore, the mono-formyl products are good precursors for soft materials which show molecular-size cavities and require de-symmetrized building blocks. As a proof of concept, methylene-alternating copolymers were prepared by reduction to corresponding alcohols and following acid-mediated condensation. The linear co-polymers show good solubility and carbon dioxide adsorption.
Keywords: formylation; building block; alternating copolymer; gas adsorption; propellane
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Kato, K.; Hiroi, T.; Okada, S.; Ohtani, S.; Ogoshi, T. Beilstein Arch. 2025, 202523. doi:10.3762/bxiv.2025.23.v1
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