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

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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 Å; 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 Å. 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 exclusively forms a resorcinol-pyrimidine O−H···N hydrogen-bonded network as above but in a different way. The resulting sheets are layered so as to give segregated columns of anthracene (I fa-a = 11.78 Å) and anthraquinone (I fq-q = 10.56 Å) which are partially overlapped with each other. Compound 1 and quinone form 1:2 (1 to quinone) adducts. An extensive 1-quinone hydrogen-bonded network in the benzoquinone adduct leads to 3-fold interpenetrating or polycatenating molecular sheets having highly slided anthracene columns (I fa-a = 3.99 Å) and quinone columns (I fq-q = 2.87 Å). The anthraquinone adduct, on the other hand, forms hydrogen-bonded one-dimensional alternate chains composed of 1 and face-to-face stacked quinone dimer. These chains are so arranged as to give segregated and partially overlapped columns for anthracene (I fa-a = 5.24 Å) and anthraquinone (I fq-q = 3.03 or 3.55 Å). It is remarkable that many of the columns are constructed via self-assembly of hydrogen-bonded one-dimensional (1D) or two-dimensional (2D) networks. The network-self-assembly strategy thus opens the door to a three-dimensional (3D) control of aromatic columns in molecular crystals, i.e., co-alignment in proximity of donor columns and acceptor columns.

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