Designed Synthesis and Crystallization of Isomorphic Molecular Gyroscopes with Cell-like Bilayer Self-Assemblies

• Published in: Crystal growth & design Vol. 18; no. 5; pp. 2795 - 2803
• Main Authors: Ochoa, Ma. Eugenia, Labra-Vázquez, Pablo, Farfán, Norberto, Santillan, Rosa
• Format: Journal Article
• Language: English
• Published: American Chemical Society 02.05.2018
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/acs.cgd.7b01542

Two molecular rotors featuring pyridine and fluorobenzene rings as polar rotators and 9-octylfluorenyl stators were synthesized. Their crystal structures were established through SXRD techniques, crystallizing in the monoclinic chiral P21 space group. The supramolecular assemblies of both isomorphs showed an orientation of static dipoles through the crystal lattice and the formation of intriguing 2D layers that resemble cell membranes, a typical example of an amphidynamic system. Small activation energies and the modulation of the first-order hyperpolarizabilities of these compounds as a function of rotational dynamics were revealed through DFT computations at the CAM-B3LYP/​M06-2X/​cc-pVDZ level of theory and correlated with a potential use of these materials as photonic switches.