A structural analysis of spiropyran and spirooxazine compounds and their polymorphs

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

Research output: Research - peer-reviewArticle

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.

LanguageEnglish
Article number84
JournalCrystals
Volume7
Issue number3
DOIs
StatePublished - 13 Mar 2017

Fingerprint

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

Keywords

  • Crystal engineering
  • Crystal structure
  • Photochromic compounds
  • Spirooxazine
  • Spiropyran

Cite this

@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",
doi = "10.3390/cryst7030084",
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.

In: Crystals, Vol. 7, No. 3, 84, 13.03.2017.

Research output: Research - peer-reviewArticle

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

VL - 7

JO - Crystals

T2 - Crystals

JF - Crystals

SN - 2073-4352

IS - 3

M1 - 84

ER -