期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 31, 页码 12197-12219出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja204366b
关键词
-
资金
- National Science Foundation [DMR-0548559, DMR-0520020, DMR-1066116, DMS-0935165]
- P. Roy Vagelos Chair at Penn
- ACS Division of Organic Chemistry (Roche)
- German Research Foundation (DFG) [SFB 625, Se 1008/55]
- Ministry of Education, Science and Technology [R31-10013]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1120901] Funding Source: National Science Foundation
- Division Of Mathematical Sciences
- Direct For Mathematical & Physical Scien [0935165] Funding Source: National Science Foundation
The synthesis of perylene 3,4:9,10-tetracarboxylic acid bisimides (PBIs) dendronized with first-generation dendrons containing 0 to 4 methylenic units (m) between the imide group and the dendron, (3,4,5)12G1-m-PBI, is reported. Structural analysis of their self-organized arrays by DSC, X-ray diffraction, molecular modeling, and solid-state H-1 NMR was carried out on oriented samples with heating and cooling rates of 20 to 0.2 degrees C/min. At high temperature, (3,4,5)12G1-m-PBI self-assemble into 2D-hexagonal columnar phases with intracolumnar order. At low temperature, they form orthorhombic (m = 0, 2, 3, 4) and monoclinic (m = 1) columnar arrays with 3D periodicity. The orthorhombic phase has symmetry close to hexagonal. For m = 0, 2, 3, 4,they consist of tetramers as basic units. The tetramers contain a pair of two molecules arranged side by side and another pair in the next stratum of the column, turned upside-down and rotated around the column axis at different angles for different m. In contrast, for m = 1, there is only one molecule in each stratum, with a four-strata 21 helical repeat. All molecules face up in one column, and down in the second column, of the monoclinic cell. This allows close and extended pi-stacking, unlike in the disruptive up-down alteration from the case of m = 0, 2, 3, 4. Most of the 3D structures were observed only by cooling at rates of 1 degrees C/min or less. This complex helical self-assembly is representative for other classes of dendronized PBIs investigated for organic electronics and solar cells.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据