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タイトル: | Conjugated double helices via self-dimerization of α,α′-dianilinotripyrrins |
著者: | Umetani, Masataka Tanaka, Takayuki https://orcid.org/0000-0001-8018-7984 (unconfirmed) Osuka, Atsuhiro |
著者名の別形: | 梅谷, 将隆 田中, 隆行 大須賀, 篤弘 |
発行日: | 1-Jan-2018 |
出版者: | Royal Society of Chemistry |
誌名: | Chemical Science |
巻: | 9 |
開始ページ: | 6853 |
終了ページ: | 6859 |
抄録: | A new motif for artificial double helices was developed on the basis of α, α′-disubstituted tripyrrin. α, α′-Dibromotripyrrin 3 was prepared by gentle bromination at the pyrrolic α-positions of 5, 10-diphenyltripyrrane followed by oxidation with DDQ. Nucleophilic substitution reactions of 3 with anilines proceeded efficiently to furnish a series of α, α′-dianilinotripyrrins 4–11, which displayed monomeric and dimeric forms depending upon the solvent used for crystallization and the structures of the substituted anilines. Dimeric forms show double helical structures with smooth π-conjugation as indicated by their absorption spectra. van't-Hoff plot analyses revealed that the dimerizations in CDCl3 are enthalpy-driven. Larger association constants of the dimerization are attained for 3, 5-di-t-butylanilino- and 3, 5-bis(trifluoromethyl)anilino-substituted tripyrrins (7 and 8) via additional multiple intermolecular interactions. In a nonpolar and aprotic solvent, tripyrrins (9 and 10) bearing bulkier 1-naphthylamino and mesitylamino groups do not dimerize but undergo unique tautomerization. |
著作権等: | © The Royal Society of Chemistry 2018. This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence. |
URI: | http://hdl.handle.net/2433/234933 |
DOI(出版社版): | 10.1039/c8sc02739k |
PubMed ID: | 30310618 |
出現コレクション: | 学術雑誌掲載論文等 |
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