Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

Oosterbaan, Wibren D.; Gerven, Paul C. M. van; Walree, Cornelis A. van; Koeberg, Mattijs; Piet, Jacob J.; Havenith, Remco W. A.; Zwikker, Jan W.; Jenneskens, Leonardus W.; Gleiter, Rolf

doi:10.1002/ejoc.200200693

Cited by 15 publications

(20 citation statements)

References 59 publications

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“…15 The procedure 20 for melt polycondensation that gave low molecular weight 1DA is described in the Supplementary Material.…”

Section: Synthesismentioning

confidence: 99%

“…A first approach to obtain polymer 1DA consisted of a melt polycondensation at 100°C of monomer 5b 15 with adipoyl chloride 4a (Scheme 2). This provided polymeric material with M w ϭ 9.5 ϫ 10 3 g mol Ϫ1 (SEC; M w /M n ϭ 1.38), equivalent to about 20 repeating units.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…UV-Vis spectra of KBr dispersions of the donoracceptor polymers and compound 3 (which is an oil) are depicted in Figure 2. Also shown is a solution spectrum of 3 in CH 2 Cl 2 , 15 which is also composed of typical N,N-dialkylanilino transitions at 257.5 and 303.5 nm. In addition to these absorptions, for 3 dispersed in KBr an absorption tail extending to 400 nm is present.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

“…16 For model compound 3 it was shown by the presence of a weak intramolecular CT absorption band that the four--bond bridge relays a weak through-bond interaction between the donor and acceptor. 15 Furthermore, in polar as well as nonpolar solvents, photoinduced intramolecular electron transfer appeared to take place in near quantitative yield. 17 The resulting charge-separated state is fluorescent in nonpolar and medium polarity solvents, but not in polar solvents like THF.…”

Section: Introductionmentioning

confidence: 97%

“…The electron donor is an N,Ndialkylanilino moiety and the electron acceptor is a 1,1-dicyanovinyl group. Photoinduced charge separation and recombination processes in a variety of compounds containing this donor-acceptor combination and a -or ---bridge have been extensively investigated by us [13][14][15] and others. 16 For model compound 3 it was shown by the presence of a weak intramolecular CT absorption band that the four--bond bridge relays a weak through-bond interaction between the donor and acceptor.…”

Section: Introductionmentioning

confidence: 99%

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Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Oosterbaan

Kaats-Richters

Jenneskens

et al. 2004

J. Polym. Sci. A Polym. Chem.

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Two high molecular weight linear polyesters were investigated to gain insight in how the photophysics of electron donor-(-spacer)-electron acceptor (DA) compounds are affected by incorporation into a polymer. They were prepared by condensation of either adipoyl or sebacoyl chloride with a diol that was functionalized with an N,N-dialkylaniline donor, a cyclohexyl type -spacer, and a 1,1-dicyanovinyl acceptor. The solubility, which is very low, and the thermal properties of the polyesters are dictated by physical crosslinking as a consequence of interchain donor-acceptor interactions. Charge transfer (CT) absorption and emission are observed, which involve CT between DA moieties of different chains rather than CT processes within a single DA unit. As a result, the photophysics of the DA units in the polyesters differs strongly from that of similar DA compounds in solution. Upon swelling the polymers with THF, the CT fluorescence disappears partly. Analogous polymers containing only an N,N-dialkylaniline donor display dual fluorescence; one band reflects local emission, while the other is attributed to excimer emission.

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“…15 The procedure 20 for melt polycondensation that gave low molecular weight 1DA is described in the Supplementary Material.…”

Section: Synthesismentioning

confidence: 99%

Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Photophysical Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Oosterbaan

Kaats-Richters

Jenneskens

et al. 2004

J. Polym. Sci. A Polym. Chem.

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Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Ikeda

Haraguchi

Numata

et al. 2007

Chemistry An Asian Journal

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We synthesized a semiartificial beta-1,3-glucan, curdlan with dialkylaniline groups (CUR-DA), that bears chromophoric aromatic groups at its peripheral positions. Spectroscopic studies as well as microscopic observations indicate that CUR-DA adopts a triple-stranded helical structure in water- or methanol-rich solutions of dimethyl sulfoxide (DMSO). This triple-stranded helical structure exhibits high thermal stability and resistance to base, attributes that are similar to those of the triple-stranded helical structure of native beta-1,3-glucans such as schizophyllan. Moreover, we found that the stability of the triple-stranded helical structure can be easily modulated by solvent composition and metal-ion (Zn2+) binding. As beta-1,3-glucan polysaccharides are known to serve as "polymeric" hosts, including certain DNA molecules, carbon nanotubes, and conjugated polymers, and complexation occurs only with the single-stranded structure, this information is very useful for the creation of these attractive polymeric composites, the controlled release of DNA, and so on.

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Efficient Synthesis of C_2v‐Symmetrical Pentakisadducts of C₆₀ as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern

Hörmann

Donaubauer

Hampel

et al. 2012

Chemistry A European J

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We report here on the selective synthesis of fullerene pentakisadducts 3 with an incomplete octahedral addition pattern by means of mixed [5:1]hexakisadducts 1 that involve an isoxazoline moiety as a protection group. The isoxazoline addend can be cleanly cleaved by irradiation with light. By using this protection-deprotection strategy, a variety of fullerene pentakisadducts 3 were synthesized in 29-44% overall yield without the need of HPLC purification. This novel photolytic deprotection of 1 can be explained by an initial electron transfer that leads to a biradical, which can easily eliminate the isoxazoline added. The very efficient and straightforward syntheses of the bisfullerene 4 and the globular hexakisadduct 7, each of which involves mixed octahedral addition patterns, clearly demonstrate the advantage of fullerene pentakisadducts 3 as suitable precursors for the construction of highly functional and complex [5:1]hexakisadduct architectures. Complete structural characterization of all new compounds was carried out by MALDI mass spectrometry, UV/Vis, FTIR, (1)H NMR and (13)C NMR spectroscopy, as well as X-ray diffraction.

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Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

Cited by 15 publications

References 59 publications

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Efficient Synthesis of C_2v‐Symmetrical Pentakisadducts of C₆₀ as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern

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Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

Cited by 15 publications

References 59 publications

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Efficient Synthesis of C2v‐Symmetrical Pentakisadducts of C60 as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern

Contact Info

Product

Resources

About

Efficient Synthesis of C_2v‐Symmetrical Pentakisadducts of C₆₀ as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern