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Synthesis of Repeating Sequence Polyaniline Derivatives

Cutler, Kenneth Allen (2009) Synthesis of Repeating Sequence Polyaniline Derivatives. Master's Thesis, University of Pittsburgh. (Unpublished)

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In order to increase solubility while maintaining conductivity, polymers incorporating periodic ortho-substituted units in the backbone of the classic para-polyaniline were prepared. The geometry of the ortho-substituted unit was postulated to allow for property enhancing substitution without the disruption -conjugation. Crucial to this goal was the protection of the ortho-diamine unit during synthetic procedures. Of the many motifs that were explored, the urea protection scheme proved to be the most amenable to the coupling reactions required to prepare segmer units with a para-ortho-para sequence. Trimeric segmers bearing 0-2 methyl substituents on the ortho-substituted unit were prepared. The substituentless and monomethyl segmers were combined with BOC-protected dimers para-aniline to yield polymers with modest molecular weights by GPC vs. polystyrene standards (Mn = 4-10 x 103, PDI ~1.5). Poor film properties prevented characterization of the conductivity properties. In an effort to identify a protecting group that would be either practically removable or more compatible with high conductivity, several motifs were explored: sulfonamides, amides, diazaboroles, diazaphosphole oxides and carbamates. All of these motifs proved unreactive to the conditions necessary to prepare the trimeric segmers analogous to those prepared from the urea. Quinoxaline and phenazine derivatives of the basic ortho-substituted unit were also prepared. While these derivatives were also difficult to incorporate into trimeric segmers, copolymers were prepared by direct coupling of phenazine units to dimeric para-substituted units. Molecular weights of these copolymers were modest, and the conductivity was found to be within one order of magnitude compared to para-polyaniline.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Cutler, Kenneth Allenkac102@pitt.eduKAC102
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairMeyer, Tara Ytmeyer@pitt.eduTMEYER
Committee MemberPetoud, Stephanespetoud@pitt.eduSPETOUD
Committee MemberChapman, Tobytchapman@imap.pitt.eduTCHAPMAN
Date: 15 January 2009
Date Type: Completion
Defense Date: 28 July 2008
Approval Date: 15 January 2009
Submission Date: 5 August 2008
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: conductivity; palladium cataylzed; phenazine; polyaniline; repeating sequence; polymer; urea
Other ID:, etd-08052008-110036
Date Deposited: 10 Nov 2011 19:57
Last Modified: 15 Nov 2016 13:48


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