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Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative

[Image: see text] This work provides a comprehensive illustration of a crystalline melt memory effect recorded for three solvates of the 2,7-bis(2-(2-methoxyethoxy)ethoxy)benzo[b]benzo[4,5] thieno[2,3-d]thiophene (OEG-BTBT) molecule with dichloromethane (DCM) molecules. Combined optical microscopy a...

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Autores principales: James, Ann Maria, Greco, Alessandro, Devaux, Félix, McIntosh, Nemo, Brocorens, Patrick, Cornil, Jérôme, Pandey, Priya, Kunert, Birgit, Maini, Lucia, Geerts, Yves Henri, Resel, Roland
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10626567/
https://www.ncbi.nlm.nih.gov/pubmed/37937189
http://dx.doi.org/10.1021/acs.cgd.3c00847
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author James, Ann Maria
Greco, Alessandro
Devaux, Félix
McIntosh, Nemo
Brocorens, Patrick
Cornil, Jérôme
Pandey, Priya
Kunert, Birgit
Maini, Lucia
Geerts, Yves Henri
Resel, Roland
author_facet James, Ann Maria
Greco, Alessandro
Devaux, Félix
McIntosh, Nemo
Brocorens, Patrick
Cornil, Jérôme
Pandey, Priya
Kunert, Birgit
Maini, Lucia
Geerts, Yves Henri
Resel, Roland
author_sort James, Ann Maria
collection PubMed
description [Image: see text] This work provides a comprehensive illustration of a crystalline melt memory effect recorded for three solvates of the 2,7-bis(2-(2-methoxyethoxy)ethoxy)benzo[b]benzo[4,5] thieno[2,3-d]thiophene (OEG-BTBT) molecule with dichloromethane (DCM) molecules. Combined optical microscopy and X-ray diffraction measurements at different temperatures are used to get an overview of the structural and morphological properties like melting points, isotropic transition temperatures, induction times, and crystallization kinetics of the three forms. An outstanding observation is made upon annealing the three polymorphs at temperatures well above their respective melting points as well as above the optical clearance temperature. After cooling back to room temperature, recrystallization results in the formation of the initial phase present before the annealing process. This melt memory effect is observed for all three solvates. These observations can be correlated to the strong interaction between the DCM molecules and the oligoethylene glycol side chains, even in the molten state. This conclusion rationalizes the experimental observation made upon solvent vapor annealing of the crystalline sample with DCM, which unambiguously transformed the system into a disordered state.
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spelling pubmed-106265672023-11-07 Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative James, Ann Maria Greco, Alessandro Devaux, Félix McIntosh, Nemo Brocorens, Patrick Cornil, Jérôme Pandey, Priya Kunert, Birgit Maini, Lucia Geerts, Yves Henri Resel, Roland Cryst Growth Des [Image: see text] This work provides a comprehensive illustration of a crystalline melt memory effect recorded for three solvates of the 2,7-bis(2-(2-methoxyethoxy)ethoxy)benzo[b]benzo[4,5] thieno[2,3-d]thiophene (OEG-BTBT) molecule with dichloromethane (DCM) molecules. Combined optical microscopy and X-ray diffraction measurements at different temperatures are used to get an overview of the structural and morphological properties like melting points, isotropic transition temperatures, induction times, and crystallization kinetics of the three forms. An outstanding observation is made upon annealing the three polymorphs at temperatures well above their respective melting points as well as above the optical clearance temperature. After cooling back to room temperature, recrystallization results in the formation of the initial phase present before the annealing process. This melt memory effect is observed for all three solvates. These observations can be correlated to the strong interaction between the DCM molecules and the oligoethylene glycol side chains, even in the molten state. This conclusion rationalizes the experimental observation made upon solvent vapor annealing of the crystalline sample with DCM, which unambiguously transformed the system into a disordered state. American Chemical Society 2023-10-16 /pmc/articles/PMC10626567/ /pubmed/37937189 http://dx.doi.org/10.1021/acs.cgd.3c00847 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle James, Ann Maria
Greco, Alessandro
Devaux, Félix
McIntosh, Nemo
Brocorens, Patrick
Cornil, Jérôme
Pandey, Priya
Kunert, Birgit
Maini, Lucia
Geerts, Yves Henri
Resel, Roland
Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title_full Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title_fullStr Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title_full_unstemmed Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title_short Memory Effect by Melt Crystallization Observed in Polymorphs of a Benzothieno-Benzothiophene Derivative
title_sort memory effect by melt crystallization observed in polymorphs of a benzothieno-benzothiophene derivative
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10626567/
https://www.ncbi.nlm.nih.gov/pubmed/37937189
http://dx.doi.org/10.1021/acs.cgd.3c00847
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