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Self‐Assembly of C 3 Symmetric Rigid Macrolactams into Very Polar and Porous Trigonal Crystals
Author(s) -
Marmin Thomas,
Dory Yves L.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900802
Subject(s) - supramolecular chemistry , crystallography , van der waals force , polar , dipole , group (periodic table) , trigonal crystal system , anisotropy , crystal (programming language) , materials science , non covalent interactions , hydrogen bond , symmetry (geometry) , chemistry , chemical physics , crystal structure , physics , geometry , molecule , optics , programming language , mathematics , organic chemistry , astronomy , computer science
Cyclohexane and cyclotri‐β‐alanyl have been used as scaffolds for the design of new C 3 ‐symmetric rings incorporating conjugated alkenes and dienes. All three C 3 ‐symmetric lactams share the same triangular shape and their crystal system is trigonal. They all belong to the R 3 space group, R 3 m , R 3 and R 3 c , for the increasingly large 12‐, 18‐ and 24‐membered rigid rings, respectively. All lactams stack on top of each other, through H‐bonds and van der Waals noncovalent interactions, leading to endless supramolecular cylinders and tubes. The largest member of the family leads to tubes, the central pores of which is wide enough to let water in. A common feature of all the lactams is their very large dipole, of around 9 D, according to DFT calculations. Surprisingly, all the resulting cylinders and tubes pack side by side in the crystals, with all the dipoles pointing to the same direction. As a result, all three crystals are anisotropic and appear to be the first members of a new kind of highly polar crystals.