Synthesis and Photophysical Property of 1-Chalcogeno-1,3-butadiene Derivatives and the Related Compounds Incorporated in a Dibenzobarrelene Skeleton

Ishii Akihiko, Nakata Norio

doi:10.5059/yukigoseikyokaishi.76.1042

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Other Title

ジベンゾバレレン骨格に組み込まれた1-カルコゲノ-1,3-ブタジエン誘導体およびその関連化合物の合成と光物性
ジベンゾバレレンコッカクニクミコマレタ 1-カルコゲノ-1,3-ブタジエンユウドウタイオヨビソノカンレンカゴウブツノゴウセイトコウブツセイ

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<p>In recent years, luminescent organic compounds including group 13—16 elements have been extensively studied from the viewpoints of applications for electronic devices and chemical sensors, in which the group 13—16 elements play an important role by providing a perturbation to the photophysical property of original hydrocarbons. We have developed dibenzobarrelene-incorporated 1-chalcogeno-1,3-butaidiene derivatives being fluorescent with high efficiency, which are synthesized by two methods; (1) the reaction of thio- or selenometallacycles with dimethyl acetylenedicarboxylate or (2) the intramolecular cycloaddition between (9-anthryl)chalcogeno and arylalkynyl groups connected by a (Z)-alkenyl group. The latter method (2) are applied to the syntheses of benzobarrelene analogues, 1-aza-1,3-butadiene analogues by cyano-Diels-Alder reaction, thiophene-fused analogues, and derivatives having π-donor and π-acceptor substituents that luminesce in the near-infrared region. In addition, we have succeeded in the synthesis of carbon and silicon analogues utilizing the intramolecular cycloaddition. In this paper, we describe the syntheses of the luminescent compounds in details with comparing their relevant and characteristic photophysical properties.</p>

Journal

Journal of Synthetic Organic Chemistry, Japan

Journal of Synthetic Organic Chemistry, Japan 76 (10), 1042-1054, 2018-10-01

The Society of Synthetic Organic Chemistry, Japan

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