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Synteza bis(pirolilo)arenów - prekursorów elektroprzewodzących polimerów

Sołoducho J.

Prace Naukowe Instytutu Chemii Organicznej, Biochemii i Biotechnologii Politechniki Wrocławskiej. Monografie

2000

Vol. 40, nr 24

55-55

Przedstawiono metody syntezy i polimeryzacji nowych pochodnych bis(pirolilo)arenów oraz wyniki badań ich przewodnictwa elektrycznego. Opracowano nową metodę syntezy bis(pirolilo)-benzenu, -naftalenu, -bifenylu, -fluorenu, -karbazolu, indolo[7,6-g]indolu, -l,4-dioksano[2,3-c]tiofenu. Wyniki tych badań w pełni wykazały, że w syntezie bis(pirolilo)arenów szczególnie użyteczna jest zmodyfikowana metoda Engela i Steglicha. Zaproponowano mechanizm reakcji cyklizacji "ylidu nitryliowego" do pochodnej bis(pirolilo)arenów, a także fluorenobis(dioksolanopropanonu) do bis(pirolilo)-fluorenu. Interesującą metodą zsyntetyzowano również układ indolo[7,6-g]indolu z 5,10-dihydroksynaftalenu. Zaproponowano mechanizm cyklizacji pochodnej naftalenu do indolo[7,6-g]indolu. Przeprowadzono wstępne badania istniejących korelacji między właściwościami fizykochemicznymi badanych połączeń a ich strukturą. Wyniki tych badań mogą znaleźć zastosowanie w projektowaniu syntez prekursorów elektroprzewodzących polimerów. Na przykładach zawartych w pracy wskazano na możliwość zastosowania tych monomerów do syntezy polimerów. Zsyntetyzowane polimery okazały się interesujące ze względu na duże przewodnictwo elektrochemiczne i dobrą stabilność. Metodologia stosowana w syntezie pirolowych monomerów i polimerów otwiera drogę do syntezy kolejnych pochodnych bis(pirolilo)arenów i ich wykorzystania w inżynierii materiałowej.

In recent years, polypyrrole and its derivatives have been widely investigated because of their easy electrosynthesis, good stability and excellent conductivity in the oxidized state. The electropolymerization of pyrrole made a significant impact in the synthesis of stable, highly conducting polymers via a relatively low oxidation potential monomers. Pyrrole oxidized at significantly lower potentials than tiophene or furan. The polymer redox processes are generally found-at 0.5 and 0.0 V vs. SCE. With this low oxidation potential to form the conducting state, the polymer is quite stable as a conductor and can be subjected to a high number of redox switches with little degradation in charge response. These properties suggest that polypyrrole may prove useful in a number of practical applications, which include areas as diverse as solid cell lithium batteries, biocompatible electrodes, and conducting textiles. The electropolymerization method has been used with great success to generate insoluble films of electrically conducting polymers on an electrode surface. Indeed, this is the principal method for the synthesis of polypyrrole and polyaniline, two polymers that have received widespread attention as "organic metals". I reported a unique synthesis of bis(pyrrol-2-yl)arenes derivatives, their electropolymerization behavior and properties of the electroactive and electrically conducting polymers obtained. The series of bis(pyrrol-2-yl)arenes were prepared by modification of the method of Engel and Steglich in accordance with the general pathway set out in Scheme 15 (synthesis of 1,4-bis(pyrrole)-arenes). The synthesis of 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene was carried out by two different procedures. Engel developed the first one in accordance to the general pathway. A second procedure for the preparation of 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene was modeled after work done by Lucchesini [21]. A comparison of both the synthetic routes revealed that the yield for bis(pyrrol-2-yl)fluorenes by the Engel method was 30% based on [86], while the yield from Lucchesini route was 20%, respectively. 1 synthesized also 3,6-bis(pyrrol-2-yl)-9-ethylcarbazole [35] and 2,5-bis(pyrrol-2-yl)dioxano-[2,3-c]thiophene, the groups of compounds developed by the Engler method. For the synthesis of 5,10-dibutoxy-indolo[7,6-g]indole, "bis(pyrrolo)naphthalene" [47], I started from 1, 5-dihydroxynaphthalene. Structures of the new compounds were confirmed by spectroscopic methods: 'H NMR, I3C NMR, HR MS. In summary, a versatile methodology for the synthesis of bis(pirrol-2-yl)arenes has been developed. The results reported herein offer a simple method of preparation of a new interesting class of compounds. The success of these methods consists in the use of simple efficient and selective reagents in every step. These procedures can be easily adapted for the synthesis of bis(pyrrol-2-yl)arenes starting from simple N,N '-diallylamides. The overall process involving simple reaction conditions and a small number of steps with generally high yields has provided convenient and valuable methods for the synthesis of bis(pyrrol-2-ylo)arenes. The introductory theoretical studies were performed in order to study relationship between structure and properties of monomers. The electropolymerization experiments with bis(pyrrole)arenes were carried out by the Dr. J. Reynolds group. A new synthetic route opens up a number of opportunities for the synthesis of potentially soluble and processable pyrrole containing polymers and is a subject of continued investigations.