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.

langue originaleAnglais
Numéro d'article84
journalCrystals
Volume7
Numéro de publication3
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

Citer ceci

@article{fc23c5e4f8a94f79891f4d391e3eabe9,
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",
month = "3",
day = "13",
doi = "10.3390/cryst7030084",
language = "English",
volume = "7",
journal = "Crystals",
issn = "2073-4352",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "3",

}

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

KW - Spirooxazine

KW - Spiropyran

UR - http://www.scopus.com/inward/record.url?scp=85015327246&partnerID=8YFLogxK

U2 - 10.3390/cryst7030084

DO - 10.3390/cryst7030084

M3 - Article

AN - SCOPUS:85015327246

VL - 7

JO - Crystals

JF - Crystals

SN - 2073-4352

IS - 3

M1 - 84

ER -