Diels-alder polymerization of a macrocyclic metal complex with p-benzoquinone

Hauschel, Bernd; Stihler, Patrick; Hanack, Michael

doi:10.1016/s0379-6779(97)80821-1

Cited by 12 publications

(8 citation statements)

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“…The search for new superstructured conjugated organic polymers [1][2][3][4][5][6][7] continues to be of interest, in particular as these systems are expected to show NLO properties, 1,2 entrap metals, [4][5][6] as well as exhibit adjustable conductivities. 7,8 With regard to these properties, electrodeposited polymers with photoisomerizable azobenzene moieties appear to be useful candidates, in particular as concerns the electronic conjugation between the chains and the functional group.…”

Section: Introductionmentioning

confidence: 99%

New conjugated polymerizable pyrrole and 2,5-dithienylpyrrole azobenzene dyes: synthesis and spectroelectrochemical properties

et al. 2003

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We describe the first easy syntheses of new fully conjugated monomers and their derived polymers containing a photoisomerizable azobenzene group, along with their electrochemical properties. Two classes of compounds have been studied differing in the nature of the polymerizable unit: pyrrole or 2, 5-dithienylpyrrole. A rather effective electronic interaction between the pyrrole and azo moieties has been demonstrated, while the conjugation is much less pronounced in the case of the terheterocycle. This behavior has been ascribed to a twisted conformation of the 2,5-dithienylpyrrole compounds in the neutral form, as demonstrated by theoretical modeling. All these molecules are electropolymerizable monomers, although the 2,5-dithienylpyrrole compounds lead only to thin films of conducting polymers when compared to their pyrrole analogs.

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Section: Introductionmentioning

confidence: 99%

New conjugated polymerizable pyrrole and 2,5-dithienylpyrrole azobenzene dyes: synthesis and spectroelectrochemical properties

et al. 2003

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“…Conjugated polymers are presently regarded as promising materials for the development of optoelectronic devices such as light-emitting diodes, photovoltaic cells, sensors, and nonlinear optical systems. , The optoelectronic properties of conjugated polymers vary significantly based upon the degree of extended conjugation between the consecutive repeat units; hence, there have been numerous syntheses of ladder-conjugated polymers for the maximization of extended π-conjugation . Other efforts to modify the optoelectronic properties of conjugated polymers have involved the construction of alternating donor/acceptor (DA) repeat units.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Conjugated Donor/Acceptor/Passivator (DAP) Polymer

Devasagayaraj

Tour

1999

Macromolecules

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A conjugated polymer is described here that possesses main-chain donor/acceptor repeat units separated by aryl passivating units. This donor/acceptor/passivator (DAP) polymer was constructed of sequential electron-rich N,N‘-dimethyl-3,4-diaminothiophene, electron-deficient 3,4-dinitrothiophene, and passivating phenylene repeat units via Stille coupling reactions. Several new transformations were conducted on thiophene cores in order to construct the monomer units: tert-butoxycarbonyl (Boc) amine protections, selective monostannylations, selective monodebrominations, lithium tetramethylpiperidide (LTMP) induced lithiation on nitrothiophenes, and selective stannylations using Bu3SnSnBu3/Pd on phenylene iodides over thienyl bromides. The Stille polymerization afforded the Boc-protected DAP polymer that was characterized at this stage. ZnCl2-catalyzed Boc removal afforded the desired DAP polymer; however, its insolubility curtailed detailed investigations of the properties.

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“…1 However, despite the great interest of the related phthalocyanine (Pc) chromophore, 2 for example as a building block for the construction of new molecular materials, the effort devoted to preparing multiphthalocyanine arrays has not been as large. The main reason could be the difficulty of preparing unsymmetric Pcs, 3 necessary for a stepwise approach to building more complex Pc systems, 4 and in the purification of Pcs 2 in comparison with porphyrins. Non-conjugated binuclear Pcs, in which the two Pc nuclei are covalently bound via various kinds of linkage, have been reported.…”

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confidence: 99%