2024-03-28T08:53:49Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/747662022-11-17T02:08:08Zhdl_2115_20045hdl_2115_139Bioinspired synthesis of pentalene-based chromophores from an oligoketone chainSaito, YukiHiguchi, MasayukiYoshioka, ShotaSenboku, HisanoriInokuma, YasuhideWe report a bioinspired synthesis of 2,5-dihydropentalene-based chromophores from an aliphatic oligoketone bearing 1,3- and 1,4-diketone subunits. Unlike the natural polyketone sequence, fused five-membered rings were formed via an intramolecular aldol condensation. A subsequent Knoevenagel condensation reaction with malononitrile furnished a multiply cross-conjugated -system with low-lying LUMO levels. Furthermore, pentalenes obtained from a non-conjugated aliphatic chain exhibited visible absorption and solid-state fluorescence.Royal Society of ChemistryJournal Articleapplication/pdfhttp://hdl.handle.net/2115/74766https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/74766/1/manuscript_revised.pdf1359-7345Chemical communications5450678867912018-06-25enginfo:doi/10.1039/c8cc02379dauthor