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New Chiral Aromatic Architectures.

Geng, Xin.

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New Chiral Aromatic Architectures.

Record Type:	Electronic resources : Monograph/item
Title/Author:	New Chiral Aromatic Architectures./
Author:	Geng, Xin.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2016,
Description:	183 p.
Notes:	Source: Dissertation Abstracts International, Volume: 78-09(E), Section: B.
Contained By:	Dissertation Abstracts International78-09B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10191388
ISBN:	9781369701821

New Chiral Aromatic Architectures.
Geng, Xin.

New Chiral Aromatic Architectures. - Ann Arbor : ProQuest Dissertations & Theses, 2016 - 183 p.

Source: Dissertation Abstracts International, Volume: 78-09(E), Section: B.

Thesis (Ph.D.)--Tulane University School of Science and Engineering, 2016.

The syntheses and structural characterization of 3-arylimino steroids, tribenzodecacyclene, hexabenzodecacyclene, and a new class of twisted chiral polycyclic aromatic compounds, the "hairpin furans" are described.

ISBN: 9781369701821Subjects--Topical Terms:

523952
Organic chemistry.

New Chiral Aromatic Architectures.
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100 1 $a Geng, Xin. $3 1278437
245 1 0 $a New Chiral Aromatic Architectures.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2016
300 $a 183 p.
500 $a Source: Dissertation Abstracts International, Volume: 78-09(E), Section: B.
500 $a Adviser: Robert Pascal.
502 $a Thesis (Ph.D.)--Tulane University School of Science and Engineering, 2016.
520 $a The syntheses and structural characterization of 3-arylimino steroids, tribenzodecacyclene, hexabenzodecacyclene, and a new class of twisted chiral polycyclic aromatic compounds, the "hairpin furans" are described.
520 $a In the hope of generating a new class of materials with large optical rotations, various arylamines were condensed with cholest-4-ene-3,6-dione (14) to give 3-arylimino steroids. These compounds possess moderately high specific rotations ([alpha]D ~ 300-800) and strong circular dichroism. One such derivative, 3-(4-methoxyphenylimino)cholest-4-en-6-one (15), crystallizes as the (E)-imine and upon dissolution undergoes mutarotation to an equilibrium mixture of ( E)- and (Z)-isomers with a half-life of approximately 1 h at room temperature, as judged by both NMR spectroscopy and polarimetry.
520 $a High-temperature, TiCl4-catalyzed, triple aldol condensations of aceanthrenone 26 and acenaphthacenone 27 gave tribenzodecacyclene 18 and hexabenzodecacyclene 19, respectively, in yields of 16% and 0.8%, respectively. Compound 18 is a red, crystalline solid that is stable under ordinary conditions; its X-ray structure reveals it to be a strongly pitched, C 3-symmetric, molecular propeller. In contrast, the more highly strained compound 19 is a blue-black solid whose solutions are unstable to air and light. Its simple NMR spectra, as well as HDFT calculations, indicated that it is a D3-symmetric molecular propeller.
520 $a The thermal reaction of two cyclopentadienones with 5,5'-binaphthoquinone or 6,6'-dimethoxy-5,5'-binaphthoquinone in refluxing nitrobenzene (210 °C) gives, in a single synthetic step that includes two Diels-Alder additions, two decarbonylations, and two dehydrogenations, giant biaryl bisquinones (compounds 42, 50, 52, 53 and 62). However, when two cyclopentadienones react with 6,6'-dimethoxy-5,5'-binaphthoquinone in nitrobenzene at higher temperatures (250--260 °C), the resulting products are molecular ribbons composed of two twisted aromatic systems fused to a heteropentahelicene (49, 51, and 54). These molecules are representatives of a new class of chiral polycyclic aromatic compounds, the "hairpin furans". Interestingly, reheating a dimethoxy-substituted giant biaryl (e.g., 52) in nitrobenzene at 260 °C does not yield the corresponding hairpin furan, and the mechanistic studies indicate that some intermediate or byproduct of the synthesis of the giant biaryls is a reagent or catalyst necessary for the conversion of the dimethoxybiaryl to the furan.
590 $a School code: 0494.
650 4 $a Organic chemistry. $3 523952
650 4 $a Chemistry. $3 516420
690 $a 0490
690 $a 0485
710 2 $a Tulane University School of Science and Engineering. $b Chemistry. $3 1669429
773 0 $t Dissertation Abstracts International $g 78-09B(E).
790 $a 0494
791 $a Ph.D.
792 $a 2016
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10191388