Article

Hexaazaphenalene derivatives: one-pot synthesis, hydrogen-bonded chiral helix, and fluorescence properties.

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.
Organic Letters (impact factor: 5.86). 10/2010; 12(21):5036-9. DOI:10.1021/ol102200v pp.5036-9
Source: PubMed

ABSTRACT Symmetric hexaazaphenalenes (R = phenyl and tert-butyl) have been synthesized by one-pot condensations of corresponding amidine hydrochlorides with tricyanomethanide. The hexaazaphenalenes are linked with each other by a N-H···N hydrogen-bonding interaction in the crystalline states. Interestingly, a planar and achiral tert-butylated derivative was crystallized in a chiral space group with assembly of one-handed helical hydrogen-bonded chains. Hexaazaphenalenyl anions were isolated as air- and water-stable tetraethyl ammonium salts.

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Keywords

achiral tert-butylated derivative
 
air-
 
chiral space group
 
corresponding amidine hydrochlorides
 
N-H···N hydrogen-bonding interaction
 
tert-butyl
 
tricyanomethanide
 
water-stable tetraethyl ammonium salts
 

Shuichi Suzuki