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Double‐Pillaring Strategy for Silacyclophanes: Synthesis and Structures of Disilanyl Double‐Pillared Bisanthracenes
Author(s) -
Nakanishi Waka,
Hitosugi Shunpei,
Shimada Yusuke,
Isobe Hiroyuki
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000543
Subject(s) - anthracene , substituent , double bond , silylation , steric effects , chemistry , crystallography , excitation , materials science , stereochemistry , photochemistry , catalysis , organic chemistry , physics , quantum mechanics
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 SiSi bonds to afford disilanyl double‐pillared bisanthracenes ( Si DPBAs). 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 .