Hydrogen-Bond-Mediated Self-Assembly of Aminopyrazolones: Macrocyclic Quartets-Single and Stacked One-Dimensional Motifs

The fab four: Aminopyrazolones which incorporate two ditopic hydrogen‐bond donor–acceptor pairs of amide and amidine functional groups can self‐assemble through formation of four hydrogen bonds. Single‐crystal X‐ray diffraction analysis reveals that homomeric aggregation (amide–amide, amidine–amidin...

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Published inAngewandte Chemie International Edition Vol. 44; no. 43; pp. 7069 - 7071
Main Authors Gong, Hegui, Krische, Michael J.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 04.11.2005
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
donor-acceptor systems
host-guest systems
Hydrogen Bonding
hydrogen bonds
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Molecular Structure
noncovalent interactions
Physical Sciences
Pyrazolones - chemical synthesis
Pyrazolones - chemistry
Science & Technology
self-assembly
DESIGN
host-guest systems
INFORMATION
RANDOM COPOLYMERS
noncovalent interactions
hydrogen bonds
SUPRAMOLECULAR CHEMISTRY
MOLECULES
self-assembly
donor-acceptor systems
FOLDAMERS
INTERFACES
SIDE-CHAIN POLYMERS
SCAFFOLDS
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Summary:The fab four: Aminopyrazolones which incorporate two ditopic hydrogen‐bond donor–acceptor pairs of amide and amidine functional groups can self‐assemble through formation of four hydrogen bonds. Single‐crystal X‐ray diffraction analysis reveals that homomeric aggregation (amide–amide, amidine–amidine) affords 1D architectures while heteromeric aggregation (amide–amidine) generates macrocyclic quartets (see picture).
Bibliography:ark:/67375/WNG-S7RVM8ZZ-T
ArticleID:ANIE200502539
istex:C14F5664EA6511D717063E659D57BD0B47334674
Acknowledgement is made to the Research Corporation Cottrell Scholar Award (CS0927), the Alfred P. Sloan Foundation, the Dreyfus Foundation, and the NSF-CAREER Program.
Acknowledgement is made to the Research Corporation Cottrell Scholar Award (CS0927), the Alfred P. Sloan Foundation, the Dreyfus Foundation, and the NSF‐CAREER Program.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502539