Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two Complementary π‑Bowls

• Published in: Crystal growth & design Vol. 18; no. 1; pp. 307 - 311
• Main Authors: Dubceac, Cristina, Sevryugina, Yulia, Kuvychko, Igor V, Boltalina, Olga V, Strauss, Steven H, Petrukhina, Marina A
• Format: Journal Article
• Language: English
• Published: American Chemical Society 03.01.2018
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/acs.cgd.7b01258

Designed synthesis of a new crystalline donor–acceptor organic hybrid has been accomplished by using two bowl-shaped polycyclic aromatic hydrocarbons (PAHs) having complementary structures and properties, namely, C20H10 and C5-C20H5(CF3)5. The X-ray structural characterization of the product, [(C20H10)­·(C20H5(CF3)5)]­·C6H4Cl2, revealed the formation of aligned columnar stacks of alternating C20H10 and C20H5(CF3)5 molecules with centroid-to-centroid distances of 3.658(8) and 3.787(8) Å and a small bowl slip of 0.086(6) Å. The tight bowl packing is accompanied by notable molecular geometry adjustments of the individual PAHs. The bowl depth increased for corannulene (Δ = +0.019 Å) and decreased for sym-pentakis­(trifluoromethyl)­corannulene (Δ = −0.011 Å), facilitating enhancement of concave–convex interactions along the stacks. The parallel alignment of one-dimensional columns is supported by multiple intermolecular interactions involving C6H4Cl2 used as the crystallization solvent, forming an infinite two-dimensional network in the solid state.