Helical polyacetylene synthesized with a chiral nematic reaction field

Science

Volumn 282, Issue 5394, 1998, Pages 1683-1686

  Akagi, K ^a   Piao, G ^a   Kaneko, S ^a   Sakamaki, K ^a   Shirakawa, H ^a   Kyotani, M ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DOPING (ADDITIVES); ELECTRIC CONDUCTIVITY; MOLECULAR STRUCTURE; NEMATIC LIQUID CRYSTALS; POLYMERIZATION; SCANNING ELECTRON MICROSCOPY; SEMICONDUCTING FILMS; SPECTRUM ANALYSIS; SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

ASYMMETRIC REACTION FIELD; CHIRAL NEMATIC LIQUID CRYSTALS; COTTON EFFECT; HELICAL POLYACETYLENES;

POLYACETYLENES;

ACETYLENE; POLYACETYLENE; TITANIUM; TITANIUM TETRA N BUTOXIDE TRIETHYLALUMINUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; ELECTRIC CONDUCTIVITY; MAGNETIC FIELD; POLYMERIZATION; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

GOSSYPIUM HIRSUTUM;

EID: 0032573485     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.282.5394.1683     Document Type: Article

References (17)

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14. D between (R)-and (S)-binol derivatives should be ascribed to an occurrence of partial racemization during the etherification reactions between the hydroxyl groups of the binaphthols and the PCH506 substituents. Because the boiling temperature of cyclohexanone, which was used as a reaction solvent, is 157°C, it is desirable that the etherification reaction be carried out by refluxing the cyclohexanone solution around 150°C. However, to obtain a higher yield, the reaction for the (S)-binol derivative was refluxed at 156°C, very close to the boiling point of cyclohexanone, and for longer times (22 hours) than in the case of the (R)-binol derivative (150°C and 14 hours). In fact, the yield (99.6%) of the (S)-binol derivative was higher than that (96.9%) of the (R)-binol derivative. However, more racemization during the etherification reaction seems to have occurred in the (S)-binol derivative than in the (R)-binol derivative.
15. Synthesis of the (R)-bino derivative shown in Scheme 3. K. Akagi, S. Kaneko, G. Piao, H. Shirakawa, M. Kyotani, unpublished results.
16. It is of keen interest that the hierarchical higher order structure observed in Fig. 5 resembles the helical self-assembled microstructure of such biological molecules as lipids. See J. M. Schnur, Science 262, 1669 (1993), and references therein.
17. This research was supported by Grant-in-Aids for Scientific Research from the Japanese Ministry of Education, Culture and Science, and in part by the Tsukuba Advanced Research Alliance (TARA) project of the University of Tsukuba.