Crystal Engineering of Stacked Aromatic Columns. Three-Dimensional Control of the Alignment of Orthogonal Aromatic Triads and Guest Quinones via Self-Assembly of Hydrogen-Bonded Networks

Abstract

We here determined the crystal structures of several adducts of the bis(resorcinol) and bis(pyrimidine) derivatives of anthracene or anthraquinone (1−3) as orthogonal aromatic triads. Anthracene-bis(resorcinol) compound 1 forms molecular sheets consisting of hydrogen-bonded homopolymeric chains of resorcinol together with anthracene stack columns having a face-to-face distance of I fa-a = 12.0−13.4 A; large supramolecular cavities left are occupied by two solvent molecules as guests via hydrogen bonding. Cocrystallization of compound 1 with anthracene-bis(pyrimidine) derivative 2 affords adduct 1·2, whose molecular sheets are composed of hydrogen-bonded resorcinol-pyrimidine alternate copolymeric chains and closer anthracene columns with I fa-a = 8.40 or 8.49 A. Columns in neighboring sheets are in a close proximity or even partially overlapped as a result of interpenetration of the sheets. Compound 1 also forms a 1:1 adduct with anthraquinone-bis(pyrimidine) derivative 3. The resulting adduct 1·3 exclusi...