TY - JOUR
T1 - Multifunctional Octamethyltetrasila[2.2]cyclophanes
T2 - Conformational Variations, Circularly Polarized Luminescence, and Organic Electroluminescence
AU - Shimada, Masaki
AU - Yamanoi, Yoshinori
AU - Ohto, Tatsuhiko
AU - Pham, Song Toan
AU - Yamada, Ryo
AU - Tada, Hirokazu
AU - Omoto, Kenichiro
AU - Tashiro, Shohei
AU - Shionoya, Mitsuhiko
AU - Hattori, Mineyuki
AU - Jimura, Keiko
AU - Hayashi, Shigenobu
AU - Koike, Hikaru
AU - Iwamura, Munetaka
AU - Nozaki, Koichi
AU - Nishihara, Hiroshi
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/8/16
Y1 - 2017/8/16
N2 - Both symmetrical and unsymmetrical cyclophanes containing disilane units, tetrasila[2.2]cyclophanes 1-9, were synthesized. The syn and anti conformations and the kinetics of inversion between two anti-isomers were investigated by X-ray diffraction and variableerature NMR analysis, respectively. The flipping motion of two aromatic rings was affected by the bulkiness of the aromatic moiety (1 vs 6), the phase (solid vs solution), and the inclusion by host molecules (1 vs 1?[Ag2L]2+). The photophysical, electrochemical, and structural properties of the compounds were thoroughly investigated. Unsymmetrical tetrasila[2.2]cyclophanes 5-8 displayed blue-green emission arising from intramolecular charge transfer. Compound 6 emitted a brilliant green light in the solid state under 365 nm irradiation and showed a higher fluorescence quantum yield in the solid state (φ = 0.49) than in solution (φ = 0.05). We also obtained planar chiral tetrasila[2.2]cyclophane 9, which showed interesting chiroptical properties, such as a circularly polarized luminescence (CPL) with a dissymmetry factor of |glum| = ca. 2 × 10-3 at 500 nm. Moreover, an organic green light-emitting diode that showed a maximum external quantum efficiency (next) of ca. 0.4% was fabricated by doping 4,4′-bis(2,2′-diphenylvinyl)-1,1′-biphenyl with 6.
AB - Both symmetrical and unsymmetrical cyclophanes containing disilane units, tetrasila[2.2]cyclophanes 1-9, were synthesized. The syn and anti conformations and the kinetics of inversion between two anti-isomers were investigated by X-ray diffraction and variableerature NMR analysis, respectively. The flipping motion of two aromatic rings was affected by the bulkiness of the aromatic moiety (1 vs 6), the phase (solid vs solution), and the inclusion by host molecules (1 vs 1?[Ag2L]2+). The photophysical, electrochemical, and structural properties of the compounds were thoroughly investigated. Unsymmetrical tetrasila[2.2]cyclophanes 5-8 displayed blue-green emission arising from intramolecular charge transfer. Compound 6 emitted a brilliant green light in the solid state under 365 nm irradiation and showed a higher fluorescence quantum yield in the solid state (φ = 0.49) than in solution (φ = 0.05). We also obtained planar chiral tetrasila[2.2]cyclophane 9, which showed interesting chiroptical properties, such as a circularly polarized luminescence (CPL) with a dissymmetry factor of |glum| = ca. 2 × 10-3 at 500 nm. Moreover, an organic green light-emitting diode that showed a maximum external quantum efficiency (next) of ca. 0.4% was fabricated by doping 4,4′-bis(2,2′-diphenylvinyl)-1,1′-biphenyl with 6.
UR - http://www.scopus.com/inward/record.url?scp=85027400038&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b05671
DO - 10.1021/jacs.7b05671
M3 - 学術論文
C2 - 28730816
AN - SCOPUS:85027400038
SN - 0002-7863
VL - 139
SP - 11214
EP - 11221
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 32
ER -