Synthesis of Some Polydiactylene Esters
Keywords:
Polydiactylene, esterAbstract
Some diacetylene ester compounds(1-13) were prepared using the well known coupling procedures. These diacetylenes monomers were polymerized by the topochenical process using UV irradiation. The resulted polymers (14-26) were found to be insoluble in all common organic solvents. The monomers were identified by IR,NMR and Mass measurements while the polymers were identified depending on their physical changes(due to insolubility ) and the identification of their oligomers by Mass and NMR measurments.
References
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Yoon, B , Lee, S and Kim, J.M (2009) Recent Conceptual and Technological Advances in Poly diacetylene-Based Supramolecular Chemo Sensors,J. Chem.Soc.Res.,38, pp1958-1968.
Charls, F. and Mary, F (1995) Experimental Organic Chemistry A Small Scale Approach, Prentice Hall Englewood cliffs, Newgersey, USA,2 ed, pp352,495.
Dafeng, L, Kun, Y, Jian, L and Xueshuu, J(2008) CuI/iodine-Mediated Homo Coupling Reaction of Terminal Alkynes to 1,3-Diynes, TetrhydronSLetts.,49, pp 5918-5919.
Dai, X,Liu, Z, , Han, B, Sun,Z, Wang,Y, Xu, J, Guo, X, Zhao, N and Chin,J (2004) Carbon Nano tube/Poly (2, 4-Hexadiyne-1, 6-Diol) Nano Composites Prepared with the Aid of Super Critical CO2, Chem. Commun., pp2190-2191.
Dewitt, H.D. and Ingersoll,A.W (1951) The Preparation of Pure N-Acetyl-L-Leucine And L-Leucine, Fur. Chem. Lab. Vand. Univ., Vol. 37, pp3359-3360.
Gilman, H (1941), Org.Syn.Coll.,Vol.1,John Wiley and sons, New York, p394.
Gros, L, Ringsdorf, H, Schupp, H and Angew, H ,(1981) Polymeric Antiumor Agents on a Molecular and on a Cellullarlevel, Chem. Int. Ed. Engl. 20, pp305-325.
Guk, E.G, Levinshtein, M.E, Marikhin,V.A, Myasnikova, L.P and Rumyantsev, S.L (1997) Electrical Properties of the Conducting Poly Diacetylene Poly-1,1 ,6,6- Tetra Phenyl Hexadiyne diamine , Phys . Sol. St., Vol.39, No.4,pp 690-694.
Horning, E.C.,(1955), Org.Syn.Coll.,Vol.3,John Wiley and sons, New York, pp(714,715),(320,321).
Huo and Russell, K.C (1999) Chromatic Studies of a Polymerizable Diacetylene Hydrogen Bonding Self-Assembly: A self-folding Process to Explain the Chromatic Change of Poly diacetylenes, Langmuir. ,Vol. 15, No.11, pp3972-3980.
Itoh, C , (1999) Optical Study On Relaxation of Excitions And Initiation of Photo Polymerization in Diacetylene Crystals at Low Temperatures, Int. J. Photo. Eng. Vol.1, pp1-5.
Jahnke, E,, Weiss, J, Neuhaus, S, Hoheisel, T.N and Frauenrath ,H (2009) Synthesis Of Diacetylene-Containing Peptide Building Blocks and Amphiphiles, their Self-Assembly and Topchemical Polymerization in Organic Solvents, Chem. Eur.J.15, pp 388-404.
Jonas, U, Shah, K, Norvez, S and Charych, D (1999) Reversible Color Switching and Unusual Polymerization of Hydrazide-Modified Poly Diacetylene Lipids, J. Am. Chem. Soc., 121, pp4580-4588.
Kuvaeva, Z.I, Lopatik ,D.V , Knizhnikova, A.N , Naidenov ,V.E and Markovich, M. M (2010), Drug Synthesis Methods and Manufacturing Technology Preparation and Use of N-Acetyl-Α-Amino Acids, J. Pharm. Chem., Vol.44, No.6, pp307-309.
Lee, H.J, Kang, S.J , Kim, K. K, Cho, H.N , Park, J.T and . Choi, S.K (1995) Synthesis and Characterization of Novel Side-Chain Nonlinear Optical Polymers Based on Poly(1,6-heptadiyne) Derivatives, Macromol. Vol.28, Issue13, pp 4638-4643.
Lewis, C.A. and Tykwinski, R.R (2006) Chiral Cross-Conjugated Iso Poly diacetylenes, Chem. Commun., pp3625-3627.
Louis, F. and Kenneth, W (1983), Organic Experimental, D.C. Health and company,Canada,5th.,ed., p306,307.
Normaa, R.,(1963), ), Org.Syn.Coll.,Vol.4, John Wiley and sons, New York, pp(715,716).
Okada, S.Y, Jelinek. K.R and Charych, D (1999) Induced Color Change of Polymeric Vesicles by Interfacial Catalysis of Phosphor Lipase, J. Chin, A(2),38, pp655-659.
Pengfei, D, Yang, G.L and Ming, H.L (2009) Preparation of Optical Active Poly Diacetylene Through Gelation & the Control of Super Molecular Chirality, Sci. Chi. Chem. Vol.35, No.2, pp432-437.
Qasim, A.A (2011) Synthesis of some streoregular and amorphous diacetylene polymers , PhD. Thesis, Mosul University.
Reppe, W. and Keyssner, E (1987) Process for Manufactu-
ring 2,4-Hexadiyne-1,6-Diol,U.S.Pat.No.4,952,292.
Sixi, H. and Neumann, W(1985) Electron-Spin-Resonance Experiments and Theory of the Butatriene-to-Acetylene Transition in Short-Chain Poly acetylene Molecules, J. Phys. Res. B. Vol. 31, Issue1, pp142-148.
Stanish, I. and Singh, A (2001) Highly Stable Vesicles Composed of a New Chain Terminus Acetylenic Photopolymer Phospholipids, Chem. Phys. Lips.,112 , pp99-108.
Stanley, R. and Wolf, K (1968), Organic functional Group Preparation ,Academic Press Inc., New York, USA,p282.
Stensuud, T, .Bernate, K.E and Johnsgaard, M (1971) Hetrocyclic Compounds from Malonyl Chlorides and Nitriles, Acta.Chem.Scand.,25,pp523-528.
Takeshi, A. and Kikamasa, S (1967) Anovel Synthesis of o-Hydroxy Benzaldehyde, Bull. Chem. Soc. Jap. Vol. 40, pp1428-1432.
Vogels, I.,(1956),A Text-Book of Practical Organic Chemistry Including Qualitative Organic Analysis, Richard clay. Ltd UK,3ed.,p423
Wyrsta, M.D , Cogen, A.L and Deming, T (2001) A Parallel Synthetic Approach for the Analysis of Membrane Interactive Copoly Peptides, J. Am. Chem. Soc., 123, pp12919-12920.
Xin-yan, W, Xiang-hong, L and Qi-lin, Z (1998) Chiral Quinolinyl-Oxazolines as Ligands for Copper(I)-Catalyzed Asymmetric Cyclopropanation, Tetrahydron. , .,9, pp 4143-4150.
Yarimoga,M.Im, Cho, Y, Kim, T.W, Jung, Y.K , Park, H.G, Lee, S and Kim, J (2010) A Color Display System Based On Thermochromic Conjugated Poly diacetylene Supramolecules, Macromol . Res., Vol. 18, No.4, pp404-407.
Yoon, B , Lee, S and Kim, J.M (2009) Recent Conceptual and Technological Advances in Poly diacetylene-Based Supramolecular Chemo Sensors,J. Chem.Soc.Res.,38, pp1958-1968.
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2013-06-30
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Al-Ajely, M. S., & Qasim, A. A. (2013). Synthesis of Some Polydiactylene Esters. Science Journal of University of Zakho, 1(1), 273–285. Retrieved from https://sjuoz.uoz.edu.krd/index.php/sjuoz/article/view/88
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