Aspects of the Photodimerization Mechanism of 2,4-Dichlorocinnamic Acid Studied by Kinetic Photocrystallography

Davaasambuu, Jav; Busse, G.; Techert, Simone

doi:10.1021/jp054723m

Cited by 39 publications

(28 citation statements)

References 34 publications

(96 reference statements)

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“…Scheme 1 a The formula of the studied compound and b the equation of the photochemical reaction proceeding in crystals of molecules in crystals [12,13]. It is worth mentioning that a decrease of diffracting power is commonly met for macromolecular crystals under the influence of synchrotron X-ray radiation used during data collection.…”

Section: Resultsmentioning

confidence: 99%

Monitoring Photochemical Reactions in Single Crystals by X-ray Diffraction: Practical Aspects

2016

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The influence of external stimuli on the decrease of crystal diffracting power and hence the quality of diffraction patterns and determined structures was studied in the case of the Norrish-Yang photochemical reaction of methyl 2-{[4-(2,4,6-triisopropylbenzoyl)benzoyl]amino}-3-phenylpropanoate, compound 1. The reaction was conducted in a single-crystal-to-single-crystal homogeneous manner. The calculated rate constant at 75°C was 1.6 9 10 -3 s -1 . In a quantitative way we illustrated a relationship between the reduction of the crystal diffracting power and the content of reactant molecules in the crystal and quantitatively showed that reactant molecules are responsible for this reduction. We observed that there is no correlation between the energy of UV-vis radiation applied to induce the photochemical reaction and the degree of the decrease of crystal diffracting power. We also showed in the case of the studied crystals that some change in temperature does not influence the degree of the decrease of the crystal diffracting power under the influence of UV-vis radiation. The unknown structures of the crystals containing pure reactant and product for compound 1 were also presented. Graphical AbstractThe influence of different external stimuli on the reduction of diffracting power of crystals was monitored quantitatively during and after the NorrishYang photochemical reaction.

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Section: Resultsmentioning

confidence: 99%

Monitoring Photochemical Reactions in Single Crystals by X-ray Diffraction: Practical Aspects

2016

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“…Separately, Kawano and coworkers have also described photochemical reactions that result in the formation of heterocyclic rings (Furusawa et al, 2007), organometallic catenation (Yamashita et al, 2007) and olefin dimerization (Takaoka et al, 2006). Techert and coworkers have also reported the structure of photodimerization reactions (Davaasumbuu et al, 2006). In a few cases, mechanistic information about reactions has also been illustrated A photograph of 100 stacked DVDs and a sugar cube.…”

Section: Results Obtained So Farmentioning

confidence: 99%

Photocrystallography

Cole

2007

Acta Cryst Sect A

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This review describes the development and application of a new crystallographic technique that is starting to enable the three-dimensional structural determination of molecules in their photo-activated states. So called 'photocrystallography' has wide applicability, particularly in the currently exciting area of photonics, and a discussion of this applied potential is put into context in this article. Studies are classified into four groups: photo-structural changes that are (i) irreversible; (ii) long-lived but reversible under certain conditions; (iii) transient with photo-active lifetimes of the order of microseconds; (iv) very short lived, existing at the nanosecond or even picosecond level. As photostructural changes relative to the 'ground state' can be subtle, this article necessarily concentrates on small-molecule single-crystal X-ray diffraction given that high atomic resolution is possible. That said, where it is pertinent, references are also made to related major advances in photo-induced macromolecular crystallography. The review concludes with an outlook on this new research area, including the future possibility of studying even more ephemeral, femtosecond-lived, photo-active species.

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“…The lifetimes τ 1 for the different samples represent the macroscopic overall transformation time of the sample to the amorphous product state for different sample thicknesses (for details see reference [9]). A possible mechanism for this reaction is proposed in Figure 15 In order to understand in more detail the possible mechanism of heterogeneous transformations, further investigations on cinnamic acid derivatives have been started [20,21].…”

Section: Photocrystallographic Studies Of Heterogeneous Photodimerisamentioning

confidence: 99%

“…COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH HOC COOH Taking into account the crystallographic results we suggest to include other dimensions of the monomer configurations in the crystal lattice [20]. In DiClCA the C=C double bonds span a small angle of 5° towards each other.…”

Section: Photocrystallographic Studies Of Heterogeneous Photodimerisamentioning

confidence: 99%

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Current developments in time-resolved X-ray diffraction

Techert

2006

Crystallography Reviews

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Aspects of the Photodimerization Mechanism of 2,4-Dichlorocinnamic Acid Studied by Kinetic Photocrystallography

Cited by 39 publications

References 34 publications

Monitoring Photochemical Reactions in Single Crystals by X-ray Diffraction: Practical Aspects

Monitoring Photochemical Reactions in Single Crystals by X-ray Diffraction: Practical Aspects

Photocrystallography

Current developments in time-resolved X-ray diffraction

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