Supramolecularly Engineered Perylene Bisimide Assemblies Exhibiting Thermal Transition from Columnar to Multilamellar Structures.
Perylene 3,4:9,10-tetracarboxylic acid bisimide (PBI) was functionalized with ditopic cyanuric acid to organize it into complex columnar architectures through the formation of hydrogen-bonded supermacrocycles (rosette) by complexing with ditopic melamines possessing solubilizing alkoxyphenyl substit...
| Publicado en: | Journal of the American Chemical Society Vol. 134; no. 18; pp. 7983 - 7995 |
|---|---|
| Autores principales: | , , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
5/9/2012
|
| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=75333124&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 75333124 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 5/9/2012 vid: 134 iid: 18 pid: 997 pub: American Chemical Society artinfo: ui: 75333124 10.1021/ja302574b ppf: 7983 ppct: 12 formats: tig: atl: Supramolecularly Engineered Perylene Bisimide Assemblies Exhibiting Thermal Transition from Columnar to Multilamellar Structures. aug: au: Yagai, Shiki Usui, Mari Seki, Tomohiro Murayama, Haruno Kikkawa, Yoshihiro Uemura, Shinobu Karatsu, Takashi Kitamura, Akihide Asano, Atsushi Seki, Shu affil: Department of Applied Chemistry & Biochemistry, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan CREST, Japan Science and Technology Agency (JST), 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan Office of Society-Academia Collaboration for Innovation, Kyoto University, Yoshida-Honmachi, Sakyo-ku, Kyoto 606-8501, Japan National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, Ibaraki 305-8562, Japan Department of Applied Chemistry & Biochemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1, Yamadaoka, Suita, Osaka 565-0871, Japan su: Clustering of particles Supramolecular chemistry Bisimides Perylene Spectrum analysis Hydrogen bonding Pi bonds (Chemistry) sug: subj: Clustering of particles Supramolecular chemistry Bisimides Perylene Spectrum analysis Hydrogen bonding Pi bonds (Chemistry) ab: Perylene 3,4:9,10-tetracarboxylic acid bisimide (PBI) was functionalized with ditopic cyanuric acid to organize it into complex columnar architectures through the formation of hydrogen-bonded supermacrocycles (rosette) by complexing with ditopic melamines possessing solubilizing alkoxyphenyl substituents. The aggregation study in solution using UV-vis and NMR spectroscopies showed the formation of extended aggregates through hydrogen-bonding and π-π stacking interactions. The cylindrical fibrillar nanostructures were visualized by microscopic techniques (AFM, TEM), and the formation of lyotropic mesophase was confirmed by polarized optical microscopy and SEM. X-ray diffraction study revealed that a well-defined hexagonal columnar (Col) structure was formed by solution-casting of fibrillar assemblies. All of these results are consistent with the formation of hydrogen-bonded PBI rosettes that spontaneously organize into the Col structure. Upon heating the Col structure in the bulk state, a structural transition to a highly ordered lamellar (Lam) structure was observed by variable-temperature X-ray diffraction, differential scanning calorimetry, and AFM studies. IR study showed that the rearrangement of the hydrogen-bonding motifs occurs during the structural transition. These results suggest that such a striking structural transition is aided by the reorganization in the lowest level of self-organization, i.e., the rearrangement of hydrogen-bonded motifs from rosette to linear tape. A remarkable increase in the transient photoconductivity was observed by the flash-photolysis time-resolved microwave conductivity (FP-TRMC) measurements upon converting the Col structure to the Lam structure. Transient absorption spectroscopy revealed that electron transfer from electron-donating alkoxyphenyl groups of melamine components to electron-deficient PBI moieties takes place, resulting in a higher probability of charge carrier generation in the Lam structure compared to the Col structure. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2012 holdings: @attributes: islocal: N |
|---|