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Australian Journal of Chemistry Australian Journal of Chemistry Society
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Synthesis of Symmetrical, Substituted (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) Monomers for Photoplastic Polymer Networks

Cornelis M. Moorhoff A , Wayne D. Cook A C , Tara Schiller A , Carl Braybrook B and San H. Thang A B
+ Author Affiliations
- Author Affiliations

A Department of Materials Engineering, Monash University, Clayton, Vic. 3800, Australia.

B Materials Science and Engineering, CSIRO, Clayton, Vic. 3168, Australia.

C Corresponding author. Email: wayne.cook@monash.edu

Australian Journal of Chemistry 65(8) 1165-1176 https://doi.org/10.1071/CH12278
Submitted: 12 June 2012  Accepted: 20 July 2012   Published: 8 August 2012

Abstract

Novel symmetrical (alkane-α,ω-diyl)(bis[3,3′-allyl dithioethers]) compounds and their ether analogues, have been synthesised from (alkane-α,ω-diyl)bis([2-{chloromethyl}allyl]sulfane) precursors, for use in crosslinked polymers which exhibit photoplastic behaviour. Facile synthesis and purification of these monomers was achieved if the alkane-α,ω-diyl moiety had at least one oxygen atom in this linker. The number of sulfur atoms in these monomers was varied from four to two to zero to produce monomers which can be used to evaluate their importance on the photoplasticity behaviour.


References

[1]  C. M. Moorhoff, W. D. Cook, F. Chen, D. Nghiem, C. Braybrook, S. Thang, J. Sun, T. F. Scott, C. N. Bowman, Aust. J. Chem. 2011, 64, 1083.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVegtL7M&md5=5356ccd0bf0a72eb19593d993ec7dad9CAS |

[2]  W. D. Cook, F. Chen, Q. D. Nghiem, T. F. Scott, C. N. Bowman, S. Chausson, L. Le Pluart, Macromol. Symp. 2010, 291, 50.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  W. D. Cook, S. Chausson, F. Chen, L. Le Pluart, C. N. Bowman, T. F. Scott, Polym. Int. 2008, 57, 469.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis12lsbc%3D&md5=3ac44248b74e8c939b16390899b75a10CAS |

[4]  T. F. Scott, A. D. Schneider, W. D. Cook, C. N. Bowman, Science 2005, 308, 1615.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltFemsL4%3D&md5=91f852668f9de460b30f39988778b549CAS |

[5]  W. D. Cook, M. Forrest, A. A. Goodwin, Dent. Mat. 1999, 15, 447.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXnvFSktb0%3D&md5=3ceaaf7d567883d7d7051119308e678aCAS |

[6]  R. E. Evans, E. Rizzardo, Macromolecules 2000, 33, 6722.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlslWktbY%3D&md5=a274a2e4c58ec95ce3e02e6da555d6e2CAS |

[7]  R. E. Evans, E. Rizzardo, J. Polym. Sci. Pol. Chem. 2001, 39, 202.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXitlam&md5=626566aca74bd7449412cf04bb1f14bdCAS |

[8]  T. F. Scott, R. B. Draughon, C. N. Bowman, Adv. Mater. 2006, 18, 2128.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XptlygsLo%3D&md5=33b85d402331c429296df88e0afb3b73CAS |

[9]  C. J. Kloxin, T. F. Scott, C. N. Bowman, Macromolecules 2009, 42, 2551.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXivFOmtbc%3D&md5=47fb5d4b2632d79f98ebcd1563b0d2d9CAS |

[10]  L. Pauling, The Nature of the Chemical Bond 1960, 3rd edn (Cornell University: New York, NY).

[11]  L. C. Allen, J. Am. Chem. Soc. 1989, 111, 9003.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXmsVSiur8%3D&md5=dfda1c68be972cd60dd063e2b6ae2843CAS |

[12]  K. Nishide, S.-i. Ohsugi, T. Miyamoto, K. Kumar, M. Node, Monatsh. Chem. 2004, 135, 189.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptVCqtw%3D%3D&md5=c83ac6935ce9c4d19fb536d16c1bd341CAS |

[13]  G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts 2008, 3rd edn (John Wiley and Sons: Sussex).