A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

Vanessa Kristina Seiler; Nikolay Tumanov; Koen Robeyns; Johan Wouters; Benoît Champagne; Tom Leyssens

doi:10.3390/cryst7030084

A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

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

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Article number	84
Journal	Crystals
Volume	7
Issue number	3
DOIs	https://doi.org/10.3390/cryst7030084
Publication status	Published - 13 Mar 2017

Funding

The authors thank Wilhelm Maximilian Hützler for helpful discussions. This work was published thanks to funding of «Actions de Recherche Concertées (ARC) de la Direction générale de l’Enseignement non obligatoire et de la Recherche scientifique-Direction de la Recherche scientifique-Communauté française de Belgique (ARC No. 15/20-068)». Part of this work has been carried out on equipment of PC2 platform of UNamur.

Funders	Funder number
Actions de Recherche Concertées
Australian Research Council
obligatoire et de la Recherche scientifique-Direction de la Recherche scientifique-Communauté française de Belgique	15/20-068

Keywords

Crystal engineering
Crystal structure
Photochromic compounds
Spirooxazine
Spiropyran

Access to Document

10.3390/cryst7030084Licence: CC BY

crystals-07-00084-v2Final published version, 10.6 MBLicence: CC BY

Cite this

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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 Beno{\^i}t Champagne and Tom Leyssens",

note = "Funding Information: The authors thank Wilhelm Maximilian H{\"u}tzler for helpful discussions. This work was published thanks to funding of «Actions de Recherche Concert{\'e}es (ARC) de la Direction g{\'e}n{\'e}rale de l{\textquoteright}Enseignement non obligatoire et de la Recherche scientifique-Direction de la Recherche scientifique-Communaut{\'e} fran{\c c}aise de Belgique (ARC No. 15/20-068)». Part of this work has been carried out on equipment of PC2 platform of UNamur. Publisher Copyright: {\textcopyright} 2017 by the authors; licensee MDPI, Basel, Switzerland.",

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AU - Seiler, Vanessa Kristina

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AU - Robeyns, Koen

AU - Wouters, Johan

AU - Champagne, Benoît

AU - Leyssens, Tom

N1 - Funding Information: The authors thank Wilhelm Maximilian Hützler for helpful discussions. This work was published thanks to funding of «Actions de Recherche Concertées (ARC) de la Direction générale de l’Enseignement non obligatoire et de la Recherche scientifique-Direction de la Recherche scientifique-Communauté française de Belgique (ARC No. 15/20-068)». Part of this work has been carried out on equipment of PC2 platform of UNamur. Publisher Copyright: © 2017 by the authors; licensee MDPI, Basel, Switzerland.

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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

KW - Spirooxazine

KW - Spiropyran

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SN - 2073-4352

VL - 7

JO - Crystals

JF - Crystals

IS - 3

M1 - 84

ER -

A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

ARC 15/20-068: Improving the Photochromism and Thermochromism in the Solid State by Co-crystallization : an Integrated Physico-chemical Approach

High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

CCDC 1529772: Experimental Crystal Structure Determination

CCDC 1529774: Experimental Crystal Structure Determination

CCDC 1529775: Experimental Crystal Structure Determination

Cite this

A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Projects

ARC 15/20-068: Improving the Photochromism and Thermochromism in the Solid State by Co-crystallization : an Integrated Physico-chemical Approach

Equipment

High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

Datasets

CCDC 1529772: Experimental Crystal Structure Determination

CCDC 1529774: Experimental Crystal Structure Determination

CCDC 1529775: Experimental Crystal Structure Determination

Cite this