1,4-Bis[(2,6-dimethoxyphenyl)ethynyl]benzene

Katsuhiko Ono,Kenichi Tsukamoto,Katsuhiro Saito,Masaaki Tomura

doi:10.1107/s1600536808013664

Abstract

The title compound, C26H22O4, is a derivative of 1,4-bis(phenylethynyl)benzene substituted by four methoxy groups at the terminal benzene rings. The asymmetric unit consists of two half-molecules; one centrosymmetric molecule is planar but the other is non-planar, with dihedral angles of 67.7 (1)° between the central benzene ring and the terminal benzene rings. In the crystal structure, molecules form a zigzag molecular network due to π–π [the interplanar and centroid–centroid distances between the benzene rings are 3.50 (1) and 3.57 (1) Å, respectively] and C—H⋯π interactions (2.75 Å). Introduction of the four methoxy groups results in the supramolecular architecture.

Highlights

The title compound, C26H22O4, is a derivative of 1,4bis(phenylethynyl)benzene substituted by four methoxy groups at the terminal benzene rings
The synthetic research of ethynylated aromatic compounds has attracted considerable attention because of interest in their molecular structures (Bunz et al, 1999; Kawase et al, 2003), optical properties (Beeby et al, 2002; Bunz, 2000) and molecular electronics (Tour, 2000). 1,4-Bis(phenylethynyl)benzene is used as a building block in applications such as liquid-crystalline materials (Dai et al, 1999) and electronconducting molecular wires (Moore et al, 2006)
We investigated the molecular and crystal structure of the title compound, (I), which is a derivative substituted by four methoxy groups at the terminal benzene rings

Summary

Crystal data

Katsuhiko Ono,a* Kenichi Tsukamoto,a Masaaki Tomurab and Katsuhiro Saitoa a Department of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, and bInstitute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan. R factor = 0.055; wR factor = 0.121; data-to-parameter ratio = 17.6. The title compound, C26H22O4, is a derivative of 1,4bis(phenylethynyl)benzene substituted by four methoxy groups at the terminal benzene rings. The asymmetric unit consists of two half-molecules; one centrosymmetric molecule is planar but the other is non-planar, with dihedral angles of. 67.7 (1) between the central benzene ring and the terminal benzene rings. Molecules form a zigzag molecular network due to – [the interplanar and centroid–. 3.57 (1) Å, respectively] and C—H interactions (2.75 Å). Introduction of the four methoxy groups results in the supramolecular architecture

Related literature

Data collection

Findings

Special details