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Updated: Feb 11, 2026

Preparation of Functional Silica Using a Bioinspired Method
Published on: August 1, 2018
Bioinspired synthesis of pentalene-based chromophores from an oligoketone chain
Yuki Saito1, Masayuki Higuchi, Shota Yoshioka
1Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan. inokuma@appchem.t.u-tokyo.ac.jp.
Abstract:
We 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 π-system with low-lying LUMO levels. Furthermore, pentalenes obtained from a non-conjugated aliphatic chain exhibited visible absorption and solid-state fluorescence.
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