Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

Autor:	Yoshinori Yamanoi, Kenichiro Omoto, Masaki Shimada, Koichi Nozaki, Tsukasa Usuki, Hiroshi Nishihara, Hikaru Koike, Daisuke Saito, Masako Kato, Munetaka Iwamura
Rok vydání:	2019
Předmět:	010405 organic chemistry Metalation Aryl Organic Chemistry Electronic structure Planar chirality 010402 general chemistry 01 natural sciences Biochemistry Fluorescence 0104 chemical sciences Crystallography chemistry.chemical_compound Planar chemistry Drug Discovery Electrophile Luminescence
Zdroj:	Tetrahedron Letters. 60:1108-1112
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2019.03.033
Popis:	Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (glum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3cf6af1a727f0c83b31726656b1c7287 https://doi.org/10.1016/j.tetlet.2019.03.033 Zobrazit plný text záznamu Full Text from ScienceDirect