Synthesis of π-Extended [1.1]Paracyclophanes, [1.1][n]PCP (n=2, 3, and 4), and Their Through-Space Conjugation.

Autor: Kayahara E; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Hirata S; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Mizuhata Y; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Yasuda Y; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Kusakabe Y; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Kaji H; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan., Yamago S; Institute for Chemical Research, Kyoto University, Uji, 611-0011, Japan.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Oct 21, pp. e202402225. Date of Electronic Publication: 2024 Oct 21.
DOI: 10.1002/chem.202402225
Abstrakt: [1.1][n]Paracyclophanes ([1.1][n]PCPs) (3) with n=2, 3, and 4, which consist of two [n]paraphenylene units connected by methylene bridges, were synthesized using short synthetic pathways with good overall yields. Single-crystal X-ray diffraction analyses reveal that the paraphenylene unit in 3 is bent, resulting in an elliptic core structure of 3. The facing bridgehead carbons of the paraphenylene units are separated by a distance much shorter than the sum of the van der Waals radii of sp 2 -carbon atoms. UV-vis absorption spectra, fluorescence spectra, electrochemical measurements, and theoretical calculations were used to demonstrate the presence of through-space (TS) conjugation in 3. Furthermore, host-guest complex formation between 3D (n=3) and tetracyanoquinodimethane in the solid state was revealed.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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