Diazadithia[7]helicenes: Synthetic Exploration, Solid-State Structure, and Properties.
Chemistry
; 19(36): 12077-85, 2013 Sep 02.
Article
en En
| MEDLINE
| ID: mdl-23873625
ABSTRACT
Diazadithia[7]helicenes were synthesized from the readily available building block ethyl 7-chloro-8-formylthieno[3,2-f]quinoline-2-carboxylate by a Wittig reaction-photocyclization strategy. The helicene core was functionalized by nucleophilic aromatic substitution with a variety of nucleophiles (e.g., O-, N-, and C-centered) and palladium-catalyzed reactions such as Suzuki coupling and Buchwald-Hartwig amination. Racemization studies confirmed that the enantiopure forms of these [7]helicenes are conformationally stable compared to their lower analogues. The solid-state structures of the novel diazadithia[7]helicenes were determined by single-crystal X-ray diffraction. The crystal structures of these azathia[7]helicenes show columnar stacking in antiparallel fashion. The HOMO-LUMO gaps of the new compounds were determined on the basis of electrochemical and optical measurements.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Compuestos Policíclicos
/
Quinolinas
/
Compuestos Aza
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2013
Tipo del documento:
Article