Thiophene-based dendronized macromonomers and polymers

Sonar, Prashant; Benmansour, Hadjar; Geiger, Thomas; Schlüter, A. Dieter

doi:10.1016/j.polymer.2007.06.024

Cited by 21 publications

(22 citation statements)

References 36 publications

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“…153 Since the initial discovery of organic compounds showing metallic conductivity, for which 2000 Nobel prize in chemistry was awarded, [154][155][156] oligo-and polythiophenes have attracted much attention as advanced molecules with practical use in electronic devices [157][158][159][160] and their potential application in field-effect transistors, 161 photovoltaic devices 162 and organic electroluminescent devices. 163 The employment of substituted 2-aminothiophenes in such areas represents the latest discovery showing a great promise in materials chemistry for the generation of novel oligo-and polythiophene structures.…”

Section: Synthesis Of Building Blocks For Optoelectronicsmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

177

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Chemistry of 2-aminothiophenes is arguably one of the most extensive and dynamic field of present-day thiophene research. Since 1961 when first report on the Gewald reaction was reported it became a universal method for synthesis of substituted 2-aminothiophenes and has gained prominence in recent times. The availability of reagents and the mild reaction conditions all contribute to the versatility of this reaction. This review summarizes the synthetic strategies for substituted 2-aminothiophenes. Consequently, details about the proposed mechanism of Gewald-like reactions and the wide scope of substituted 2-aminothiophenes for real life applications.

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Section: Synthesis Of Building Blocks For Optoelectronicsmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

177

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“…Schlüter and co-workers reported no difference between the absorption spectra of the thiophene-based macromonomers and the dendronized polymer. [16] The observed broadening in the absorption spectrum of 9 may result in the overlapping of planer dithiophene segments in 7 through the polymerization. The fluorescence maxima is redshifted by Dl = 21 nm relative to their respective macromonomers.…”

Section: Resultsmentioning

confidence: 99%

“…Schlüter and co-workers synthesized thiophenebased dendronized polymers by the polymerization of macromonomers with different-sized thiophene dendrons. [16] Herein, a series of dendronized polymers with all-thiophene dendrons were synthesized and characterized. Moreover, the electronic conductivities of dendronized polymers with different conjugated dendritic side chains were investigated.…”

Section: Introductionmentioning

confidence: 99%

Rodlike Macromolecules through Spatial Overlapping of Thiophene Dendrons

Kimura

Kitao

Fukawa

et al. 2011

Chemistry A European J

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Two novel dendritic macromonomers 7 and 8 functionalized with electroactive conjugated thiophene oligomers were synthesized by stepwise cross-coupling reactions and the introduction of a vinyl group at the focal point. Both macromonomers were polymerized into dendronized polymers 9 and 10 by using a radical polymerization method. The photophysical and redox behaviors of dendronized polymers 9 and 10 are significantly different from those of the corresponding macromonomers. This difference may result from the spatial overlapping of thiophene dendrons through π-π interactions when the dendrons are connected to a polymer backbone. The dendronized polymers can organize into large-area two-dimensional sheets with a thickness of 4.8 nm. Polymer 9, which has all-dendritic thiophene side chains, exhibited enhanced conductivity by partial doping with iodine or nitrosonium tetrafluoroborate (NOBF(4)). The novel amphiphilic dendronized polymer 15 was synthesized by the atom-transfer radical polymerization of macromonomer 7 from a poly(ethylene glycol) (PEG) macroinitiator and was found to have a self-organized structure in water.

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“…The conformational preferences of the dendron used to prepare MG2, 53 which consists of three Th rings linked by - and - linkages (3T; Scheme 1), was studied in a previous work. 52 More specifically, the potential energy surface derived from the systematic variation of the inter-ring dihedral angles was calculated at the B3LYP/6-31G(d) level.…”

Section: Mg2 and Mg3 Macromonomersmentioning

confidence: 99%

Internal organization of macromonomers and dendronized polymers based on thiophene dendrons

et al. 2015

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The internal organization of macromonomers (MGs) consisting of all-thiophene dendrons of generation g= 2 and 3 attached to a phenyl core, as well as of the dendronized polymers resulting from polymerization of these macromonomers (PG2 and PG3, respectively), has been investigated using theoretical methods. The conformational preferences of the MGs, determined using density functional theory calculations, are characterized by the relative orientation between dendrons and core.We find that the strain of the MGs increases with the generation number and is alleviated by small conformational re-arrangements of the peripheral thiophene rings.The conformations obtained for the MGs have subsequently been used to construct models for the dendronized polymers. Classical molecular dynamics simulations have evidenced that the interpenetration of dendrons belonging to different repeat units is very small for PG2. In contrast, the degree of interpenetration is found to be very high for PG3, which also shows a significant degree of backfolding (i.e. occurrence of peripheral methyl groups approaching the backbone). Consequently, PG2 behaves as a conventional linear flexible polymer bearing bulk pendant groups, whereas PG3 is better characterized as a semirigid homogenous cylinder. The two polymers are stabilized by - stacking interactions, even though these are significantly more abundant for PG3 than for PG2; the average number of interactions per repeat unit is 3.0 and 8.8 for PG2 and PG3, respectively. While in these interactions the thiophene rings can adopt either parallel (sandwich) or perpendicular (T-shaped) dispositions, the former scenario turns out to be the most abundant.3

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Thiophene-based dendronized macromonomers and polymers

Cited by 21 publications

References 36 publications

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Rodlike Macromolecules through Spatial Overlapping of Thiophene Dendrons

Internal organization of macromonomers and dendronized polymers based on thiophene dendrons

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