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Chemistry - Organic Chemistry | Hierarchical Bottom-Up Methodology for Integrating Dynamic Ethynylhelicene… - Synthesis,

Hierarchical Bottom-Up Methodology for Integrating Dynamic Ethynylhelicene Oligomers

Synthesis, Double Helix Formation, and the Higher Assembly Formation

Series: Springer Theses

Saito, Nozomi

2013, XII, 89 p. 72 illus., 45 illus. in color.

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  • Nominated by Tohoku University as an outstanding Ph.D. thesis
  • Describes methodology to systematically obtain diverse synthetic homo- and hetero-double helix molecules using ethynylhelicene oligomers
  • Brings to the reader’s attention unprecedented studies on assembly formation formed by intercomplex interaction of synthetic double helices

In biological systems, molecules hierarchically form ordered assemblies and macroscopic substances, as exemplified by the assembly of proteins. The development of such systems using oligomeric macromolecules obtained by organic synthesis can provide insights into biological phenomena and will lead to the creation of new materials. In this regard, synthetic double helix molecules are attractive subjects of study because they have an important structural motif  that appears widely in nature and can exhibit dynamic structural change. This thesis describes an unprecedented bottom-up approach using synthetic ethynylhelicene oligomers, which form dynamic double helices in organic media. Oligomer synthesis, homo- and hetero-double helix formation, and higher assembly formation due to intercomplex interactions are documented. The hierarchical assembly formation is a cogent reminder of the assembly of biological proteins that create living creatures. Also notable here is the demonstration of a methodology of providing diverse hetero-double helices and their higher assemblies by changing the combination of oligomers, which can be another advantage of this synthetic system.

Content Level » Research

Keywords » Bottom-up Approach - Chiral Discrimination - Double Helix - Helicene - Oligomeric Macromolecules - Pseudoenantiomer

Related subjects » Nanotechnology - Organic Chemistry - Polymer Science

Table of contents 

Introduction: Hierarchical Bottom-Up Methodology for Integrating.- Synthesis of Ethynylhelicene Oligomers.- Oligomers Possessing

Branched Alkyloxycarbonyl Side Chains.- Oligomers Possessing Perfluorooctyl Side Chains.- Oligomers Possessing Alternating

Decyloxycarbonyl/Perfluorooctyl Side Chains.- Homo-Double Helix Formation of Ethynylhelicene Oligomers Possessing Various

Side Chains.- Oligomers Possessing Decyloxycarbonyl Side Chains.- Oligomers Possessing Branched Alkyloxycarbonyl Side

Chains.- Oligomers Possessing Perfluorooctyl Side Chains.- Oligomers Possessing Decylthio Side Chains.- Oligomers Possessing

Alternating Decyloxycarbonyl/Perfluorooctyl Side Chains.- Summary of Effect of Side Chains on Stability of Homo-Double Helices.-

Hetero-Double Helix Formation of Pseudoenantiomeric Ethynylhelicene Oligomers.- (P)-D-5/(P)-F-5 Systems.- (M)-D-5/(P)-F-5

Systems.- (M)-bD-4/(P)-D-5 Systems.- (M)-D-n/(P)-DF-n Systems.- Summary.- Higher Assembly Formation of Pseudoenantiomeric

Ethynylhelicene Oligomers.- Fiber/Gel Formation in Toluene.- Vesicle Formation in Diethyl Ether.- Higher Assembly Formation by

Intercomplex Interactions.- Summary.- Conclusions.- Experimental Section

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