A Perylene Bisimide Organogelator for Chlorinated Solvents. Issue 2 (29th January 2014)

• Record Type: Journal Article
• Authors: Lin, Xu; Hirono, Misaki; Kurata, Hiroki; Seki, Tomohiro; Maruya, Yukihiro; Nakayama, Ken‐ichi; Yagai, Shiki
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 2(2014:Feb.)
• Page Start: 128
• Page End: 132
• Publication Date: 2014-01-29
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201300252
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 CHCl₃ and 1, 1, 2, 2‐tetrachloroethane (TCE), but it gave viscous solutions in CCl₄ 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 CCl₄ whereas it exists as monomeric or at least oligomeric species in CHCl₃ 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 CCl₄ solution, we fabricated top contact organic field effect transistors. The devices showed <italic>n</italic>‐type semiconductivity with a mobility of 1.5×10⁻⁵ cm² V⁻¹ s⁻¹.</p> </abstract>