A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

Vanessa Kristina Seiler, Nikolay Tumanov, Koen Robeyns, Johan Wouters, Benoit Champagne, Tom Leyssens

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6′-nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8′-methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.

langueAnglais
Numéro d'article84
journalCrystals
Volume7
Numéro3
Les DOIs
étatPublié - 13 mars 2017

Empreinte digitale

Polymorphism
structural analysis
Structural analysis
Hydrogen bonds
Oxazines
Functional groups
Evaporation
Crystal structure
evaporation
Single crystals
interactions
hydrogen bonds
X ray diffraction
crystal structure
Molecules
single crystals
hydrogen
diffraction
molecules
x rays

mots-clés

    Citer ceci

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    title = "A structural analysis of spiropyran and spirooxazine compounds and their polymorphs",
    abstract = "In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6′-nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8′-methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.",
    keywords = "Crystal engineering, Crystal structure, Photochromic compounds, Spirooxazine, Spiropyran",
    author = "Seiler, {Vanessa Kristina} and Nikolay Tumanov and Koen Robeyns and Johan Wouters and Benoit Champagne and Tom Leyssens",
    year = "2017",
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    doi = "10.3390/cryst7030084",
    language = "English",
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    journal = "Crystals",
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    publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
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    A structural analysis of spiropyran and spirooxazine compounds and their polymorphs. / Seiler, Vanessa Kristina; Tumanov, Nikolay; Robeyns, Koen; Wouters, Johan; Champagne, Benoit; Leyssens, Tom.

    Dans: Crystals, Vol 7, Numéro 3, 84, 13.03.2017.

    Résultats de recherche: Contribution à un journal/une revueArticle

    TY - JOUR

    T1 - A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

    AU - Seiler,Vanessa Kristina

    AU - Tumanov,Nikolay

    AU - Robeyns,Koen

    AU - Wouters,Johan

    AU - Champagne,Benoit

    AU - Leyssens,Tom

    PY - 2017/3/13

    Y1 - 2017/3/13

    N2 - In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6′-nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8′-methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.

    AB - In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6′-nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8′-methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.

    KW - Crystal engineering

    KW - Crystal structure

    KW - Photochromic compounds

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    KW - Spiropyran

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