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A Perylene Bisimide Organogelator for Chlorinated Solvents
Author(s) -
Lin Xu,
Hirono Misaki,
Kurata Hiroki,
Seki Tomohiro,
Maruya Yukihiro,
Nakayama Kenichi,
Yagai Shiki
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300252
Subject(s) - perylene , chemistry , monomer , supramolecular chemistry , polymer , intermolecular force , transmission electron microscopy , fluorescence , atomic force microscopy , chemical engineering , organic chemistry , nanotechnology , photochemistry , molecule , materials science , physics , quantum mechanics , engineering
Dye‐incorporated gel‐like materials are an attractive functional soft matter for optoelectronic applications. Chlorinated solvents are commonly used for the development of organic devices. Herein, we report that a perylene‐bisimide‐functionalized flexible bisurea can work as an efficient organogelator for several chlorinated solvents. The bisurea formed organogels in CHCl 3 and 1,1,2,2‐tetrachloroethane (TCE), but it gave viscous solutions in CCl 4 at millimolar concentrations. UV/vis and fluorescence spectroscopies, atomic force microscopy, and transmission electron microscopy observation of the diluted solutions revealed that the bisurea forms soluble supramolecular polymers in CCl 4 whereas it exists as monomeric or at least oligomeric species in CHCl 3 and TCE at micromolar concentrations. These results suggest that differences in the aggregation process could explain the gelation behavior in chlorinated solvents. By using a viscous CCl 4 solution, we fabricated top contact organic field effect transistors. The devices showed n ‐type semiconductivity with a mobility of 1.5×10 −5 cm 2 V −1 s −1 .