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Discrete π‐Stacks from Self‐Assembled Perylenediimide Analogues
Author(s) -
Su Feng,
Chen Guangmei,
Korevaar Peter A.,
Pan Fangfang,
Liu Huijiao,
Guo Zongxia,
Schenning Albertus P. H. J.,
Zhang HuiJun,
Lin Jianbin,
Jiang YunBao
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201907838
Subject(s) - tetramer , supramolecular chemistry , stacking , dimer , crystallography , chemistry , nuclear magnetic resonance spectroscopy , self assembly , spectroscopy , alkyl , chemical physics , materials science , stereochemistry , crystal structure , nanotechnology , physics , organic chemistry , enzyme , quantum mechanics
The formation of well‐defined finite‐sized aggregates represents an attractive goal in supramolecular chemistry. In particular, construction of discrete π‐stacked dye assemblies remains a challenge. Reported here is the design and synthesis of a novel type of discrete π‐stacked aggregate from two comparable perylenediimide (PDI) dyads ( PEP and PBP ). The criss‐cross PEP ‐ PBP dimers in solution and ( PBP ‐ PEP )‐( PEP ‐ PBP ) tetramers in the solid state are well elucidated using single‐crystal X‐ray diffraction, dynamic light scattering, and diffusion‐ordered NMR spectroscopy. Extensive π–π stacking between the PDI units of PEP and PBP as well as repulsive interactions of swallow‐tailed alkyl substituents are responsible for the selective formation of discrete dimer and tetramer stacks. Our results reveal a new approach to preparing discrete π stacks that are appealing for making assemblies with well‐defined optoelectronic properties.