期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 7, 页码 2258-2271出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902416
关键词
chirality; desymmetrization; discotics; liquid crystals; self-assembly
资金
- EU Marie Curie Intra-European [MEIF-CT-2006-042044]
- NRSC-Catalysis Institute
Two novel nonsymmetrical disc-shaped molecules 1 and 2 based on 3,3'-bis(acylamino)-2,2'-bipyridine units were synthesized by means of a statistical approach. Discotic 1 possesses six chiral dihydrocitronellyl tails and one peripheral phenyl group, whereas discotic 2 possesses six linear dodecyloxy tails and one peripheral pyridyl group. Preorganization by strong intramolecular hydrogen bonding and subsequent aromatic interactions induce self-assembly of the discotics. Liquid crystallinity of 1 and 2 was determined with the aid of polarized optical microscopy, differential scanning calorimetry, and X-ray diffraction. Two columnar rectangular mesophases (Col(r)) have been identified, whereas for C-3-symmetrical derivatives only one Col(r) mesophase has been found.([1]) In solution, the molecularly dissolved state in chloroform was studied with H-1 NMR spectroscopy, whereas the self-assembled state in apolar solution was examined with optical spectroscopy. Remarkably, these desymmetrized discot ics, which lack one aliphatic wedge, behave similar to the symmetric parent compound. To prove that the stacking behavior of discotics 1 and 2 is similar to that of reported C-3-symmetrical derivatives, a mixing experiment of chiral 1. with C-3-symmetrical 13 has been undertaken; it has shown that they indeed belong to one type of self-assembly. This helical J-type self-assembly was further confirmed with UV/Vis and photoluminescence (PL) spectroscopy. Eventually, disc 2, functionalized with a hydrogen-bonding acceptor moiety, might perform secondary interactions with molecules such as acids.
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