We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
7,7,8,8-Tetraaryl- o-quinodimethane Stabilized by Dibenzo Annulation: A Helical π-Electron System That Exhibits Electrochromic and Unique Chiroptical Properties.
- Authors
Suzuki, Takanori; Sakano, Yuto; Iwai, Tomohiro; Iwashita, Shinichi; Miura, Youhei; Katoono, Ryo; Kawai, Hidetoshi; Fujiwara, Kenshu; Tsuji, Yasushi; Fukushima, Takanori
- Abstract
When two benzene rings are fused to a tetraaryl- o-quinodimethane skeleton, sterically hindered helical molecules 1 acquire a high thermodynamic stability. Because the tetraarylbutadiene subunit contains electron-donating alkoxy groups, 1 undergo reversible two-electron oxidation to 22+, which can be isolated as deeply colored stable salts. Intramolecular transfer of the point chirality (e.g., sec-butyl) on the aryl groups to helicity induces a diastereomeric preference in dications 2 b2+ and 2 c2+, which represents an efficient method for enhancing circular-dichroism signals. Thus, those redox pairs can serve as new electrochiroptical response systems. X-ray analysis of dication 22+ revealed π-π stacking interaction of the diarylmethylium moieties, which is also present in solution. The stacking geometry is the key contributor to the chirosolvatochromic response.
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 1, p117
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201203092