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64 Pages·2017·3.298 MB·English
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SPRINGER BRIEFS IN MOLECULAR SCIENCE Pradip K. Dutta Vinod Kumar Optically Active Polymers A Systematic Study on Syntheses and Properties 123 SpringerBriefs in Molecular Science More information about this series at http://www.springer.com/series/8898 Pradip K. Dutta Vinod Kumar (cid:129) Optically Active Polymers A Systematic Study on Syntheses and Properties 123 PradipK.Dutta VinodKumar Department ofChemistry Department ofChemistry Motilal Nehru National Institute Motilal Nehru National Institute ofTechnology ofTechnology Allahabad, Uttar Pradesh Allahabad, Uttar Pradesh India India ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs inMolecular Science ISBN978-981-10-2605-8 ISBN978-981-10-2606-5 (eBook) DOI 10.1007/978-981-10-2606-5 LibraryofCongressControlNumber:2016950887 ©TheAuthor(s)2017 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpart of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission orinformationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfrom therelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authorsortheeditorsgiveawarranty,expressorimplied,withrespecttothematerialcontainedhereinor foranyerrorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper ThisSpringerimprintispublishedbySpringerNature TheregisteredcompanyisSpringerNatureSingaporePteLtd. Theregisteredcompanyaddressis:152BeachRoad,#22-06/08GatewayEast,Singapore189721,Singapore Preface Recently, the ranking of world institutions has been the front page news to all academicians, researchers, students and industrialists. Nowadays, innovation and constructive research are required in every field to survive globally. As a result, researchhasgainedremarkablemomentumineveryaspectofscience,engineering, technologyandsocialsciences.Allnationsoftheworldarefocusingonneed-based research for further development. Research is the sense of mind, imagination and creation of a person which enumerates the results or shape to the reality. In true sense, research has multi-dimensional phases and approaches. Like in general, a physicistshouldprefertoworkonphysicsroute,achemistonchemistryandsoon. Buttherearemanyareaswhicharecompositeinnature,whereitneedsmulti-talent expertise and it is only possible from researchers of various disciplines. Optically activepolymersaresuchmaterialswhereapersonofdifferentfieldsofresearchcan work.Tocarryoutadvancedstudiesorpresentneed-basedresearch,itismandatory tounderstandthematerialfirst.Opticallyactivematerialscanrotateintoaplaneof polarization and its activity originates from the presence of chiral elements in a polymersuchaschiralcentresorchiralaxesduetolong-rangeconformationalorder in a macromolecule. Surprisingly, most naturally occurring macromolecules pos- sess the ability to organize to more complex high structure rather than single one and manifest their functions. The problems of charged and reactive polymers are correlatedtoopticallyactivecompoundsanditshowsaninherent property ofboth ordinary macromolecules and large range of synthetic polymers. It is true that the properties of a material depend on the synthesis methods. Hence to know all such characteristics, a good researcher should begin the study of optically active poly- mers in a systematic manner like from synthesis to property. The present brief entitled “Optically active polymers: A systematic study on syntheses and proper- ties” is an attempt to provide the researchers of various backgrounds with a thor- ough understanding and knowledge of the optically active polymers with a special emphasis on syntheses and properties. We sincerely thank all learned researchers v vi Preface whose works have been the major source motivation for the preparation of this brief. We are also thankful to the editorial board and publisher for accepting our proposal. Allahabad, India Pradip K. Dutta May 2016 Vinod Kumar Acknowledgement Wegratefullyacknowledgetheresearchenvironmentsupportprovidedtousinthe Department of Chemistry of the Institute during the preparation of the manuscript. Theauthorsalsoexpresstheirgratitudetovariousauthorsofdifferentliteratureand researcherswhoseworkshavebeentheessential sourceandsupporttopreparethe manuscript in its present form. vii About the Book The brief presents a systematic study of synthesis of optically active polymers. It discusses in detail about the syntheses of three different types of optically active polymers from helical polymers, dendronized polymers and other types of poly- meric compounds. The brief also explains the syntheses of optically active azoaromatic and carbazole containing azoaromatic polymers and copolymers; optically active benzodithiophene; and optically active porphyrin derivatives. The final chapter of the brief discusses different properties of optically active polymers such as nonlinear optical properties, chiroptical properties, vapochromic behavior, absorption and emission properties, fabrication and photochromic properties. The intrinsicdetailsofdifferentpropertiesofopticallyactivepolymerswillbeusefulfor researchers and industry personnel, who are actively engaged in application ori- ented investigations. ix Contents Optically Active Polymers: A Systematic Study on Syntheses and Properties. .... .... .... ..... .... .... .... .... .... ..... .... 1 1 Introduction .... .... .... ..... .... .... .... .... .... ..... .... 1 2 Synthesis of Optically Active Polymers.... .... .... .... ..... .... 2 2.1 Helical Polymer .... ..... .... .... .... .... .... ..... .... 2 2.2 Poly (ethyl L-lysinimide)s.. .... .... .... .... .... ..... .... 4 2.3 Poly (ethyl L-lysinamide)s.. .... .... .... .... .... ..... .... 4 2.4 Optically Active Poly(amide–imide)s . .... .... .... ..... .... 4 2.5 Poly(phenylacetylene)..... .... .... .... .... .... ..... .... 9 2.6 Optically Active Dendronized Polymers... .... .... ..... .... 9 2.7 Optically Active Poly(ester-imide)s [33]... .... .... ..... .... 10 2.8 Optically Active Polyalkylthiophenes [34–37] .. .... ..... .... 10 2.9 Synthesis of Optically Active Azoaromatic and Carbazole Containing Azoaromatic Polymers and Copolymers.. ..... .... 14 2.10 Synthesis of Optically Active Benzodithiophene Based Poly(aryleneethynylene)s for Solar Cells [71]... .... ..... .... 21 2.11 Synthesis of Optically Active Porphyrin Derivatives Bearing Four Chiral Citronellal Moieties .. .... .... ..... .... 25 2.12 Asymmetric Polymerizations of N-Substituted Maleimides Bearing L-Leucine Ester Derivatives .... ..... .... 26 3 Characterization Techniques for Analyzing the Optical Activities of Polymers .... ..... .... .... .... .... .... ..... .... 29 4 Properties.. .... .... .... ..... .... .... .... .... .... ..... .... 31 4.1 Nonlinear Optical Properties of Azo-Polymers .. .... ..... .... 31 4.2 Thermal Analysis ... ..... .... .... .... .... .... ..... .... 34 4.3 Chiroptical Properties ..... .... .... .... .... .... ..... .... 35 4.4 Vapochromic Behaviour... .... .... .... .... .... ..... .... 35 4.5 Absorption and Emission Properties.. .... .... .... ..... .... 36 4.6 Thermosensitivity ... ..... .... .... .... .... .... ..... .... 37 xi

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