Cyclization from Higher Excited States of Diarylethenes Having a Substituted Azulene Ring

被引：2

作者：

Hattori, Yohei ^{[1
]}

Maejima, Tatsuya ^{[1
]}

Sawae, Yumi ^{[1
]}

Kitai, Jun-ichiro ^{[1
]}

Morimoto, Masakazu ^{[2
,3
]}

Toyoda, Ryojun ^{[4
]}

Nishihara, Hiroshi ^{[4
]}

Yokojima, Satoshi ^{[5
]}

Nakamura, Shinichiro ^{[6
]}

Uchida, Kingo ^{[1
]}

机构：

[1] Ryukoku Univ, Fac Sci & Technol, Dept Mat Chem, Otsu, Shiga 5202194, Japan

[2] Rikkyo Univ, Dept Chem, Toshima Ku, 3-34-1 Nishi Ikebukuro, Tokyo 1718501, Japan

[3] Rikkyo Univ, Res Ctr Smart Mol, Toshima Ku, 3-34-1 Nishi Ikebukuro, Tokyo 1718501, Japan

[4] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

[5] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

[6] RIKEN Cluster Sci Technol & Innovat Hub, Nakamura Lab, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 50期

基金：

日本科学技术振兴机构;

关键词：

azulene; cyclization; density functional calculations; electronic structures; photochromism; substituent effects; IRREVERSIBLE PHOTOCHROMIC SYSTEMS; MOLECULAR-ORBITAL METHODS; MIXED-CRYSTALS; LIGHT; DITHIENYLETHENES; ABSORPTION; PHOTOCYCLIZATION; THERMOCHEMISTRY; DERIVATIVES; SWITCHES;

D O I：

10.1002/chem.202001671

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cyclization reaction of diarylethenes having an azulene ring occurs only via higher excited states. Novel diarylethenes having an azulene ring with a strong donor or acceptor were synthesized and examined in these reactions. A derivative having an electron-donating 1,3-benzodithiol-2-ylidenemethyl group at the 1-position of the azulene ring showed photochromism, whereas neither a derivative having a pi-conjugated electron-donating group at the 3-position of the azulene ring nor derivatives having a pi-conjugated electron-withdrawing group at the 1- or 3-position of the azulene ring showed any photochromism. The photoreactivities of these compounds were explained by calculating forces and bond orders on the excited states using density functional theory (DFT) and time-dependent (TD)-DFT.

引用

页码：11441 / 11450

页数：10

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