Dynamic behavior, electrochromism, and two-photon absorption of dicyanomethylenated quinacridone.
J Org Chem
; 79(20): 9669-77, 2014 Oct 17.
Article
en En
| MEDLINE
| ID: mdl-25254634
ABSTRACT
Molecular structures of dicyanomethylenated quinacridone (1) as a solid and in solution were examined on the basis of single-crystal X-ray structural analysis, temperature-dependent (1)H NMR in CD2Cl2, and theoretical calculations. Crystal 1 had a curved, butterfly-shaped molecular structure. Thermally activated flipping between the curved, butterfly-shaped structure and an armchair structure occurred in solution. Electrochemical reduction triggered a dynamic change from the curved, butterfly-shaped conformation in the neutral state to a planar conformation in the dianion state, which represented electrochromic behavior with electrochemical bistability. A large two-photon absorption cross section of compound 1 was observed in the resonance-enhancement region of 423 GM (1 GM = 1 × 10(-50) cm(4) s photon(-1) molecule(-1)) at 710 nm. Multiple donor-acceptor charge-transfer pathways of molecule 1 enhanced two-photon absorption.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Compuestos Heterocíclicos de 4 o más Anillos
/
Nitrilos
Idioma:
En
Revista:
J Org Chem
Año:
2014
Tipo del documento:
Article
País de afiliación:
Japón