Alphabet-Inspired Design of (Hetero)Aromatic Push-Pull Chromophores

• Published in: Chemical record Vol. 16; no. 4; pp. 1886 - 1905
• Main Authors: Klikar, Milan, Solanke, Parmeshwar, Tydlitát, Jiří, Bureš, Filip
• Format: Journal Article
• Language: English
• Published: United States Blackwell Publishing Ltd 01.08.2016; Wiley Subscription Services, Inc
• Subjects: Benzene; chromophores; conjugation; donor-acceptor systems; Optics; photochemistry; structure-activity relationships; chromophores; donor-acceptor systems; structure-activity relationships; photochemistry; conjugation
• ISSN: 1527-8999; 1528-0691; 1528-0691
• DOI: 10.1002/tcr.201600032

Push–pull molecules represent a unique and fascinating class of organic π‐conjugated materials. Herein, we provide a summary of their recent extraordinary design inspired by letters of the alphabet, especially focusing on H‐, L‐, T‐, V‐, X‐, and Y‐shaped molecules. Representative structures from each class were presented and their fundamental properties and prospective applications were discussed. In particular, emphasis is given to molecules recently prepared in our laboratory with T‐, X‐, and Y‐shaped arrangements based on indan‐1,3‐dione, benzene, pyridine, pyrazine, imidazole, and triphenylamine. These push–pull molecules turned out to be very efficient charge‐transfer chromophores with tunable properties suitable for second‐order nonlinear optics, two‐photon absorption, reversible pH‐induced and photochromic switching, photocatalysis, and intercalation. Make your ABCs: Current organic push–pull molecules can be inspired by letters of the alphabet. These extraordinary arrangements involve H‐, L‐, T, V‐, X‐, and Y‐shaped molecules in particular. In this personal account, selected representatives of each class, their fundamental properties, and perspective applications are reviewed. Recent donor–π–acceptor molecules adopting T, X, and Y shapes are emphasized.