Helical growth of semiconducting columnar dye assemblies based on chiral perylene bisimides.
A perylene bisimide derivative bearing two phenyl substituents with chiral solubilizing alkyl chains at the imide N atoms has been synthesized, and its self-assembly properties in solution and condensed phase have been investigated. Temperature-dependent CD spectra revealed the coexistence of two different kinds of chiral aggregates, differing in size and handedness. The chiral side chains effect a higher order within the self-assemblies, resulting in an increased charge-carrier mobility in the columnar liquid crystalline mesophase. [structure: see text]
Dehm
Volker
V
Institut für Organische Chemie and Röntgen Research Center for Complex Material Systems, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.
Chen
Zhijian
Z
Baumeister
Ute
U
Prins
Paulette
P
Siebbeles
Laurens D A
LD
Würthner
Frank
F
D000473:Alkanes / Q000737:chemistry; D002942:Circular Dichroism; D004396:Coloring Agents / Q000138:chemical synthesis*; D019281:Dimerization; D007094:Imides / Q000138:chemical synthesis*; D008956:Models, Chemical; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012666:Semiconductors; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013696:Temperature
D000473:Alkanes; D004396:Coloring Agents; D007094:Imides; C510697:perylene bisimide; D010569:Perylene