synthesis of monomers for new conjugated polymers

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synthesis of monomers for new conjugated polymers university of massachusetts amherst scholarworks@umass amherst masters theses 1911 - february 2014 2012 synthesis of monomers for new conjugated polymers kedar girish jadhav university of massachusetts amherst follow this and additional works at: https://scholarworks.umass.edu/theses part of the organic chemistry commons this thesis is brought to you for free and open access by scholarworks@umass amherst. it has been accepted for inclusion in masters theses 1911 - february 2014 by an authorized administrator of scholarworks@umass amherst. for more information, please contact scholarworks@library.umass.edu. jadhav, kedar girish, "synthesis of monomers for new conjugated polymers" (2012). masters theses 1911 - february 2014. 753. retrieved from https://scholarworks.umass.edu/theses/753 https://scholarworks.umass.edu?utm_source=scholarworks.umass.edu%2ftheses%2f753&utm_medium=pdf&utm_campaign=pdfcoverpages https://scholarworks.umass.edu/theses?utm_source=scholarworks.umass.edu%2ftheses%2f753&utm_medium=pdf&utm_campaign=pdfcoverpages https://scholarworks.umass.edu/theses?utm_source=scholarworks.umass.edu%2ftheses%2f753&utm_medium=pdf&utm_campaign=pdfcoverpages http://network.bepress.com/hgg/discipline/138?utm_source=scholarworks.umass.edu%2ftheses%2f753&utm_medium=pdf&utm_campaign=pdfcoverpages https://scholarworks.umass.edu/theses/753?utm_source=scholarworks.umass.edu%2ftheses%2f753&utm_medium=pdf&utm_campaign=pdfcoverpages mailto:scholarworks@library.umass.edu synthesis of monomers for new conjugated polymers a thesis presented by kedar girish jadhav submitted to the graduate school of the university of massachusetts amherst in partial fulfillment of the requirements for the degree of master …

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_______________________________________ d. venkataraman, chair _______________________________________ paul m. lahti, member ______________________________________ craig t. martin, department head chemistry dedicated to my parents v acknowledgement i take this immense opportunity to express my deep sense of gratitude and reverence to my research advisor prof. d. venkataraman, for his keen interests, inspiring guidance, and invaluable suggestions towards this project work. he has been a source of inspiration, motivation and encouragement. his personal touch is an examplenary quality of a great human being. i would like to thank my committee member prof. paul lahti who has been co-operative, and provided me with good research insights and feedback. i would like to thank my collaborators, prof. jayant kumar at umass lowell for their contribution. i will like to thank other faculty members of chemistry department for their kind cooperation. i will like to thank the non-teaching staff of chemistry staff for facilitating other work. i must …

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thesis addresses the problem of synthesis of different monomers for donor and acceptor polymers in photovoltaic applications. in general, functionalization of conjugated polymers and understanding of molecular packing of electron donors and electron acceptors are very important to produce efficient solar cells. as a result, it is important to design and synthesize novel monomers which will require making new π- conjugated donors and acceptors polymers and understand the influence of these new polymers in bulk heterojunction to design polymer solar cells. in this study, two different monomers were synthesized. the first monomer was designed and synthesized to investigate the effect of π-conjugated linker directly attached to the polymer backbone where the polymer backbone was based on thiophene unit and conjugated linker was 1,2,3-triazole. in a different study, a conjugated monomer based on benzthiadiazole was designed and synthesized in order to synthesize new acceptor homopolymers and alternating copolymers. two different monomers …

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...18 2.6 fluorescence quenching with pcbm………………………………………….19 2.7 characterization………………………………………………………………..19 2.8 problems associated with monomer synthesis………………………………...21 viii 2.9 conclusion and future work…………………………………………………24 2.10 experimental details………………………………………………………...25 2.11 references…………………………………………………………………...35 3.synthesis of new conjugated acceptor monomers and polymers based on benzthiadiazole…………………………………41 3.1 introduction…………………………………………………………………... 41 3.2 molecular design and synthesis………………………………………………44 3.3 characterization of monomers………………………………………………...48 3.4 uv-vis studies and cyclic voltametry………………………………………..48 3.5 characterization of alternating copolymers…………………………………..51 3.5.1 uv-vis absorption studies and cyclic voltametry………………………51 3.5.2 mobility studies…………………………………………………………..52 3.6 future work and directions……………………………………………………52 3.7 experimental details…………………………………………………………..53 3.8. references……………………………………………………………………64 biblography……………………………………………………………………..69 ix list of tables table page 3.1 molecular weight and energy levels for polymer pbtd 1 and pbtd 2……... 49 3.2 molecular weight and energy levels for polymer pbtdv 1 and pbtdv 2…..51 x list of figures figure page 1.1 schematic representation of operating principle of a photovoltaic cell. ...................... 2 1.2 structures of monomer m1, m2 and polymer p3tzt ................................................. 7 1.3 structures of monomer 1, monomer 2, homopolymers …

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for monomer 1 ............................................................................ 16 2.5 synthesis scheme for monomer 2 .............................................................................. 17 2.6 polymer synthesis from monomer 2 ......................................................................... 18 2.7 1h nmr of monomer 1 ............................................................................................. 20 2.8 1h nmr of monomer 2 ............................................................................................. 21 2.9 synthesis of compound 6 using cui/dipea method................................................ 22 2.10 1h nmr of click reaction product (compound 6) using cui/dipea method…………………………………………………………………………………...22 2.11 synthesis of compound 6 using cuso4/sodium ascorbate method ........................ 23 2.12 1h nmr of click reaction product using cuso4/sodium ascorbate method……………………………………………………………………………………24 3.1 energy levels for donor and acceptor materials. dotted lines indicate tunable energy levels for acceptor ............................................................................................................. 42 xi 3.2 synthesis scheme for monomer 1(m1) used for making pbtd & pbtdv polymers………………………………………………………………………………….45 3.3 synthesis of polymer pbtd 1 from m1 .................................................................... 46 3.4 synthesis scheme for compound 5-8 ........................................................................ 47 3.5 iodination of compound 8 ......................................................................................... 47 3.6 synthesis of polymer pbtd 2 from m2 .................................................................... 48 3.7 synthesis of …

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synthesis of monomers for new conjugated polymers university of massachusetts amherst scholarworks@umass amherst masters theses 1911 - february 2014 2012 synthesis of monomers for new conjugated polymers kedar girish jadhav university of massachusetts amherst follow this and additional works at: https://scholarworks.umass.edu/theses part of the organic chemistry commons this thesis is brought to you for free and open access by scholarworks@umass amherst. it has been accepted for inclusion in masters theses 1911 - february 2014 by an authorized administrator of scholarworks@umass amherst. for more information, please contact scholarworks@library.umass.edu. jadhav, kedar girish, "synthesis of monomers for new conjugated polymers" (2012). masters theses 1911 - february 2014. 753. retrieved fr...

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