Evidence for the expulsion of bis-CO from bridged α-diketones

Strating, J.; Zwanenburg, B.; Wagenaar, Anno; Udding, A.C.

doi:10.1016/s0040-4039(01)87489-x

Cited by 92 publications

(68 citation statements)

References 16 publications

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“…Extensive irradiation, typically >1 h at 2.1 mW, results in the quantitative conversion of the dkDDOA solution into a DDOA gel. 1 H‐NMR spectroscopy of dkDDOA in CDCl 3 shows that the photoconversion occurs without side‐product formation as previously reported for other diketo‐anthracene derivatives (Figure S6, Supporting Information). This particularly compensates for the moderate quantum yield of photodecarbonylation in DMSO (Φ R‐468nm = 2%), which is lower than in toluene (Φ R‐468nm = 14%) due to competitive population of nonreactive stabilized charge‐transfer excited states in the polar solvent .…”

Section: Resultssupporting

confidence: 75%

Photocontrolled Hierarchical Self‐Assembly of Anisotropic Micropatterns of Nanofibers onto Isotropic Surfaces

Vet

Gartzia‐Rivero

Schäfer

et al. 2020

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Hierarchical self‐assembly is achieved using a visible light triggered photoreaction. A pro‐gelator, α‐diketone‐2,3‐didecyloxyanthracene, is photoconverted into a low molecular weight gelator, 2,3‐didecyloxyanthracene (DDOA), that self‐assembles into nanofibers. Spatial confinement and patterns of these nanofibers onto a surface are achieved by localizing initial nucleation with a focused laser and photogenerate subsequent fiber growth with the laser or gentler wide‐field irradiation. Remarkably, collective growth of nanofibers results in anisotropic micropatterns with orientation factors (OF) reaching 79%, resulting in collective emission of linearly polarized light. The OF, distance of collective growth and fiber density, are controlled by the photoirradiation conditions and the balance of interactions between DDOA aggregates and the glass surface. An unprecedented juxtaposition of orthogonally oriented nanofiber patterns on an isotropic surface is achieved with individual control of the fibers' main direction. In perspective, this photochemical method can be extended to a large variety of self‐assembling molecules.

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Section: Resultssupporting

confidence: 75%

Photocontrolled Hierarchical Self‐Assembly of Anisotropic Micropatterns of Nanofibers onto Isotropic Surfaces

Vet

Gartzia‐Rivero

Schäfer

et al. 2020

Small

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“…This group used the Strating-Zwanenburg [49] reaction, i.e., the photobisdecarbonylation of the bridged α-diketone 37 [50,51], in a PMMA matrix (Fig. 13) [48].…”

Section: Parent Heptacenementioning

confidence: 99%

Beyond Pentacenes: Synthesis and Properties of Higher Acenes

Tönshoff

Bettinger

2013

Polyarenes I

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Acenes consist of linearly annulated benzene rings. Their reactivity increases quickly with increasing chain length. Therefore acenes longer than pentacene are very sensitive towards oxygen in the presence of light and thus these molecules have not been well studied or have remained elusive in spite of synthetic efforts dating back to the 1930s. This review gives an historical account of the development of the chemistry of acenes larger than pentacene and summarizes the recent progress in the field including strategies for stabilization of higher acenes up to nonacene.

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“…Our approach relies upon a protecting-group strategy based on the photochemically induced bisdecarbonylation of bridged a-diketones, sometimes called the Strating-Zwanenburg reaction. [16] This reaction has been used for acene synthesis previously, [16,17] most notably by Neckers and co-workers for the synthesis of hexacene (1, x = 6) and heptacene (2) in PMMA. [6,18] In our experiments, the photobisdecarbonylation is performed at 30 K in an argon matrix that stabilizes the reactive acene.…”

mentioning

confidence: 99%