title: Discrete stacking of aromatic oligoamide macrocycles.
abstract: Unlike the precise structural control typical of closed assemblies, curbing the stacking of disc- and ring-shaped molecules is quite challenging. Here we report the discrete stacking of rigid aromatic oligoamide macrocycles 1. With increasing concentration, the aggregation of 1 quickly plateaus, forming a discrete oligomer, as suggested by 1D (1)H, 2D nuclear Overhauser effect, and diffusion-ordered NMR spectroscopy. Quantum-chemical calculations indicate that the tetramer of 1 is the most stable among oligomeric stacks. X-ray crystallography revealed a tetrameric stack containing identical molecules adopting two different conformations. With a defined length and an inner pore capable of accommodating distinctly different guests, the tetramers of 1 densely pack into 2D layers. Besides being a rare system of conformation-regulated supramolecular oligomerization, the discrete stacks of 1, along with their higher-order assemblies, may offer new nanotechnological applications.
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Xiangxiang
authors.initials: X
authors.lastname: Wu
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.|‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Rui
authors.initials: R
authors.lastname: Liu
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Bharathwaj
authors.initials: B
authors.lastname: Sathyamoorthy
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Yamato
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Guoxing
authors.initials: G
authors.lastname: Liang
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Lin
authors.initials: L
authors.lastname: Shen
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Sufang
authors.initials: S
authors.lastname: Ma
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Dinesh K
authors.initials: DK
authors.lastname: Sukumaran
authors.affiliation: ‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Thomas
authors.initials: T
authors.lastname: Szyperski
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Weihai
authors.initials: W
authors.lastname: Fang
authors.affiliation: §National Institute for Food and Drug Control, Beijing 100050, China.
authors.forename: Lan
authors.initials: L
authors.lastname: He
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Xuebo
authors.initials: X
authors.lastname: Chen
authors.affiliation: †Key Laboratory of Theoretical and Computational Photochemistry of the Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.|‡Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States.
authors.forename: Bing
authors.initials: B
authors.lastname: Gong
mesh_terms: D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D000577:Amides; D047028:Macrocyclic Compounds