Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers
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 formylati...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2025-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.21.95 |
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| Summary: | 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 monoformyl products are good precursors for soft materials which show molecular-size cavities and require desymmetrized building blocks. As a proof of concept, methylene-alternating copolymers were prepared by reduction to corresponding alcohols followed by acid-mediated condensation. The linear copolymers show good solubility and carbon dioxide adsorption. |
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| ISSN: | 1860-5397 |