From branched hydrocarbon propellers to C3-symmetric graphite disks

被引：78

作者：

Wu, JS ^{[1
]}

Tomovic, Z ^{[1
]}

Enkelmann, V ^{[1
]}

Müllen, Y ^{[1
]}

机构：

[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 16期

关键词：

D O I：

10.1021/jo049452a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Branched hydrocarbon propellers (9 and 12) were prepared by stepwise palladium-catalyzed Hagihara-Sonogashira coupling reactions and Diels-Alder cycloadditions and submitted to oxidative cyclodehydrogenation by FeCl3 to afford two new giant graphite disks 2 and 3 with 3-fold symmetry in high yield. One of the precursors, the polyphenylene dendrimer 9 containing 150 carbon atoms, was crystallographically characterized. The poorly soluble graphite disks were characterized by isotope-resolved MALDI-TOF mass spectroscopy, and their electronic and vibrational properties were investigated by solid-state UV-vis and Raman spectroscopy. The effect of molecular size and geometry on their properties was discussed. The molecule 2 represents the largest, 3-fold-symmetric all-benzenoid graphite disk, and the five-membered rings in molecule 3 open the opportunity to synthesize large bowl-shaped PAHs.

引用

页码：5179 / 5186

页数：8

共 54 条

[11] Interpretation of Raman spectra of disordered and amorphous carbon [J].