Synthesis and Chemical Properties of Conjugated Polyacetylenes Having Pendant Fullerene and/or Porphyrin Units

Lu, Fushen; Xiao, Shengqiang; Li, Yuliang; Liu, Huibiao; Hong-mei, LI; Zhuang, Jian; Liu, Yang; Wang, Ning; He, Xiaorong; Li, Xiaofang; Gan, Liangbing; Zhu, Daoben

doi:10.1021/ma0490045

Cited by 40 publications

(28 citation statements)

References 54 publications

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“…Because highly cis-stereoregular polyacetylenes commonly exhibit relatively sharp resonances for the vinylene protons, it seems that the cis-content of poly (2) is lower than that of the polymers that were obtained by polymerization with Rh catalysts. [44][45][46][47] This conclusion was also supported by the presence of IR absorption peaks at ñ = 1276 (s) and 901 cm À1 (w), which were assigned to a trans structure, as well as a peak at ñ = 742 cm À1 (m) that was assigned to a cis structure (see the Supporting Information, Figure S3). [48] Poly (3)-poly(6) showed trends in their 1 H NMR and IR spectra that were similar to those of poly (2).…”

Section: Resultsmentioning

confidence: 80%

Synthesis of End‐Functionalized Polyacetylenes that Contain Polar Groups by Employing Well‐Defined Palladium Catalysts

Castanon

Kuwata

Shiotsuki

et al. 2012

Chemistry A European J

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A series of [(dppf)PdBr(R)]-type complexes (dppf=1,1'-bis(diphenylphosphino)ferrocene; R=p-cyanophenyl (1 a), o-hydroxymethylphenyl (1 b), and triphenylvinyl (1 c)), in combination with silver trifluoromethanesulfonate (AgOTf), were demonstrated to be active for the polymerization of monosubstituted polar acetylene monomers HC≡CCONHC(4)H(9) (2), HC≡CCO(2)C(8)H(17) (3), HC≡CCH(2)OCONHC(6)H(13) (4), HC≡CCH(2)OCO(2)C(6)H(13) (5), and HC≡CCH(CH(3))OH (6). The yields and molecular weights of the polymers depended on the combination of the Pd catalyst and monomer that was employed. Matrix-assisted laser-desorption/ionization-time of flight (MALDI-TOF) mass spectrometric analysis indicated the formation of polymers that contained the "R" and "H" groups at the chain ends. IR spectroscopic analysis supported the R-end-functionalization of the polymers. NMR spectroscopy and MS identified the presence of species that were formed by single, double, and triple insertion of the monomers into the Pd-C(6)H(4)-p-CN bond, thereby giving solid evidence for an insertion mechanism for the present system. Density functional theory (DFT) calculations suggested the preference for 1,2-insertion of the monomer compared to 2,1-insertion.

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Section: Resultsmentioning

confidence: 80%

Synthesis of End‐Functionalized Polyacetylenes that Contain Polar Groups by Employing Well‐Defined Palladium Catalysts

Castanon

Kuwata

Shiotsuki

et al. 2012

Chemistry A European J

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“…The porphyrin 1 [6] and the azide derivative 2·4 PF 6 [7] of cyclobis(paraquat-p-phenylene) were prepared following literature procedures.…”

Section: General Informationmentioning

confidence: 99%

Photoinduced Electron Transfer within a Zinc Porphyrin–Cyclobis(paraquat‐p‐phenylene) Donor–Acceptor Dyad

Fathalla

Barnes

Young

et al. 2014

Chemistry A European J

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Understanding the mechanism of efficient photoinduced electron-transfer processes is essential for developing molecular systems for artificial photosynthesis. Towards this goal, we describe the synthesis of a donor-acceptor dyad comprising a zinc porphyrin donor and a tetracationic cyclobis(paraquat-p-phenylene) (CBPQT(4+) ) acceptor. The X-ray crystal structure of the dyad reveals the formation of a dimeric motif through the intermolecular coordination between the triazole nitrogen and the central Zn metal of two adjacent units of the dyad. Photoinduced electron transfer within the dyad in MeCN was investigated by femtosecond and nanosecond transient absorption spectroscopy, as well as by transient EPR spectroscopy. Photoexcitation of the dyad produced a weakly coupled ZnP(+.) -CBPQT(3+.) spin-correlated radical-ion pair having a τ=146 ns lifetime and a spin-spin exchange interaction of only 0.23 mT. The long radical-ion-pair lifetime results from weak donor-acceptor electronic coupling as a consequence of having nine bonds between the donor and the acceptor, and the reduction in reorganization energy for electron transfer caused by charge dispersal over both paraquat units within CBPQT(3+.) .

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“…Moreover, it is expected that attaching side electroactive groups to the well defined π-conjugated system (77) will improve the light-harvesting capacity and charge separation efficiency for potential applications in solar cells. In this regard, several polyacetylene-based DC bearing fullerene and zinc-porphyrin, (ZnP) (67), (68 a-c) (78,79), fullerene and perylenebisimide (69) (80) or only fullerene as the pendant groups have been prepared and investigated (Fig. 24).…”

Section: Double-cable Polymersmentioning

confidence: 99%

Fullerene Polymers: Synthetic Strategies, Properties and Applications

Giacalone

Martı́n

2007

Encyclopedia of Polymer Science and Technology

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A general overview of the different C 60 ‐containing polymers according to their chemical structure and the general synthetic routes followed for their preparation as well as their potential applications is presented. The many fullerene‐containing polymers reported in the recent literature have been classified depending upon the position of the fullerenes within the polymer chain and considering the type of chemical connectivity between them. The combination of fullerenes and polymer chemistry is a new interdisciplinary field in which all the knowledge on the synthesis and study of natural, as well as artificial macromolecules, can be applied to fullerenes to achieve novel fullerene‐based architectures. The combination of the unique properties of C 60 with the characteristics of well‐known polymers, often allow chemists to create new materials with combined features. In some cases, novel unprecedented properties open the doors to new realistic applications. In this article, a general overview of the different types of C 60 ‐containing polymers according to their chemical structure and the consideration of their general synthetic routes as well as their plausible applications is given. The aim of this work is to establish a classification of the many fullerene‐containing polymers reported in the literature in order to clarify the field for all those chemists interested in the topic. Nevertheless to say that not all the examples known are covered, but those more representative or appealing for the authors. For a more comprehensive presentation the readers are referred to a recent review on the same topic.

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Synthesis and Chemical Properties of Conjugated Polyacetylenes Having Pendant Fullerene and/or Porphyrin Units

Cited by 40 publications

References 54 publications

Synthesis of End‐Functionalized Polyacetylenes that Contain Polar Groups by Employing Well‐Defined Palladium Catalysts

Synthesis of End‐Functionalized Polyacetylenes that Contain Polar Groups by Employing Well‐Defined Palladium Catalysts

Photoinduced Electron Transfer within a Zinc Porphyrin–Cyclobis(paraquat‐p‐phenylene) Donor–Acceptor Dyad

Fullerene Polymers: Synthetic Strategies, Properties and Applications

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