Bis(10‐methylacridinium)s as a Versatile Platform for Redox‐Active Functionalized Dyes and Novel Structures. Issue 1 (21st November 2014)

• Record Type: Journal Article
• Authors: Suzuki, Takanori; Takeda, Takashi; Ohta, Eisuke; Wada, Kazuhisa; Katoono, Ryo; Kawai, Hidetoshi; Fujiwara, Kenshu
• Is Part Of: Chemical record. Volume 15:Issue 1(2015:Feb.)
• Page Start: 280
• Page End: 294
• Publication Date: 2014-11-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/tcr.201402073
• Languages: English
• ISSNs: 1527-8999

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>10‐Methylacridinium is a stable aromatic cation exhibiting yellow‐orange color and strong green fluorescence (FL), and can be used as a versatile building block in constructing a wide variety of novel π‐electron systems. The dications with the two chromophores connected by a proper π spacer undergo reversible "dyrex" (dynamic redox) behavior, and C–C bond formation/cleavage is accompanied by their redox reactions. The prototype is biphenyl‐2, 2′‐diylbis(10‐methylacridinium), which exhibits electrochromic response with ON/OFF switching of FL during the reversible interconversion with the di(spiroacridan)‐type electron donor. Slight structural alteration under the concept of "MFMS" (maximum function on the minimum skeleton) endowed the dyrex system with metal‐binding or chiroptical properties, which could be modified by the redox reactions. Some of the di(spiroacridan) derivatives generated from bis(10‐methylacridinium)s have extreme structural parameters, such as the greatest C–C bond length ever reported.</p> </abstract>