Helicenes, which consist of ortho-annulated aromatic or heteroaromatic rings having screw-shaped structures, are known as intriguing, intrinsically chiral frameworks, and are intensively studied in wide ranges of areas, including materials sciences, chiroptical devices, and asymmetric synthesis.1 Among helicenes, thiahelicenes are unique thanks to the presence of thiophene rings, which confer special chemical, geometric, and electronic features.2 For several years, we have been interested in the study of the synthesis and functionalization of thiahelicenes, such as tetrathiahelicene (7-TH) derivatives (Figure 1), that are a class of configurationally stable heterohelicenes, potentially very interesting for applications in optoelectronics,3 catalysis,4 and biology.5 Moreover, these systems can be easily functionalized at the 2 and 13 positions of the two terminal thiophene rings, allowing the modulation of the chemical and physical properties. Despite all these potential advantages, most of the synthetic methodologies to prepare 7-TH derivatives involve oxidative photochemical cyclization processes, which require specific equipment, highly diluted solutions, and long reaction times. Recently, we have developed a versatile non-photochemical procedure for the synthesis of functionalized thiahelicenes, thus making available a class of variously substituted compounds.
|Titolo:||Chiral thiophene-based helicenes: versatile tools in organic chemistry|
|Data di pubblicazione:||22-set-2016|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Enti collegati al convegno:||Società Chimica Italiana|
|Citazione:||Chiral thiophene-based helicenes: versatile tools in organic chemistry / S. Cauteruccio, D. Dova, E. Licandro. ((Intervento presentato al 37. convegno Convegno della Divisione di Chimica Organica tenutosi a Mestre nel 2016.|
|Appare nelle tipologie:||14 - Intervento a convegno non pubblicato|