TY - JOUR
T1 - Double-pillaring strategy for silacyclophanes
T2 - Synthesis and structures of disilanyl double-pillared bisanthracenes
AU - Nakanishi, Waka
AU - Hitosugi, Shunpei
AU - Shimada, Yusuke
AU - Isobe, Hiroyuki
N1 - Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.
PY - 2011/2/1
Y1 - 2011/2/1
N2 - A new series of silacyclophanes with two disilanyl pillars has been synthesized using a straightforward method. A silylation reaction of 1,8-dilithioanthracenes allowed the connection of two anthracene rings with two Si-Si bonds to afford disilanyl double-pillared bisanthracenes ( SiDPBAs). The major product had an anti geometry of the anthracene rings, and a unique steplike structure favorable for σ-π conjugations was revealed by X-ray crystallographic analysis. Upon introducing a substituent at the 10-position of anthracene, we obtained a U-shaped isomer with syn geometry that yielded an excimer upon excitation and can decompose without steric protection. Easy access to silacyclophanes: A new series of silacyclophanes, disilanyl double-pillared bisanthracenes (SiDPBAs), was synthesized using a one-pot operation from 1,8-diiodoanthracenes. The major product with anti geometry bears a steplike structure favorable for σ-π conjugation, and the minor product with syn geometry bears a U-shaped structure favorable for excimer formation.
AB - A new series of silacyclophanes with two disilanyl pillars has been synthesized using a straightforward method. A silylation reaction of 1,8-dilithioanthracenes allowed the connection of two anthracene rings with two Si-Si bonds to afford disilanyl double-pillared bisanthracenes ( SiDPBAs). The major product had an anti geometry of the anthracene rings, and a unique steplike structure favorable for σ-π conjugations was revealed by X-ray crystallographic analysis. Upon introducing a substituent at the 10-position of anthracene, we obtained a U-shaped isomer with syn geometry that yielded an excimer upon excitation and can decompose without steric protection. Easy access to silacyclophanes: A new series of silacyclophanes, disilanyl double-pillared bisanthracenes (SiDPBAs), was synthesized using a one-pot operation from 1,8-diiodoanthracenes. The major product with anti geometry bears a steplike structure favorable for σ-π conjugation, and the minor product with syn geometry bears a U-shaped structure favorable for excimer formation.
KW - arenes
KW - cyclophanes
KW - macrocycles
KW - silanes
KW - substituent effects
UR - http://www.scopus.com/inward/record.url?scp=79251519958&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79251519958&partnerID=8YFLogxK
U2 - 10.1002/asia.201000543
DO - 10.1002/asia.201000543
M3 - Article
C2 - 20936665
AN - SCOPUS:79251519958
VL - 6
SP - 554
EP - 559
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 2
ER -