Self-Assembled Pd(II) Barrels as Containers for Transient Merocyanine Form and Reverse Thermochromism of Spiropyran

Self-assembly of a cis-blocked Pd­(II) 90° ditopic acceptor [cis-(tmeda)­Pd­(NO3)2] (M) with a tetradentate donor L 1 [benzene-1,4-di­(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N,N,N′N′-tetramethylethane-1,2-diamine]. Exclusive formation...

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Published inJournal of the American Chemical Society Vol. 140; no. 25; pp. 7952 - 7960
Main Authors Howlader, Prodip, Mondal, Bijnaneswar, Purba, Prioti Choudhury, Zangrando, Ennio, Mukherjee, Partha Sarathi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.06.2018
Amer Chemical Soc
Subjects
ambient temperature
Chemistry
Chemistry, Multidisciplinary
dimethyl sulfoxide
heat
irradiation
isomers
nitrates
Physical Sciences
Science & Technology
solids
ultraviolet radiation
PHOTOCHROMIC PROPERTIES
MEMORIES
COMPLEX
PHOTOISOMERIZATION
ISOMERIZATION
GUEST-BINDING
CAGES
DIARYLETHENES
EXCHANGE
DERIVATIVES
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Abstract Self-assembly of a cis-blocked Pd­(II) 90° ditopic acceptor [cis-(tmeda)­Pd­(NO3)2] (M) with a tetradentate donor L 1 [benzene-1,4-di­(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N,N,N′N′-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
AbstractList Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [ cis-(tmeda)Pd(NO ) ] (M) with a tetradentate donor L [benzene-1,4-di(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N, N, N' N'-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [ cis-(tmeda)Pd(NO3)2] (M) with a tetradentate donor L1 [benzene-1,4-di(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N, N, N' N'-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [ cis-(tmeda)Pd(NO3)2] (M) with a tetradentate donor L1 [benzene-1,4-di(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N, N, N' N'-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [cis-(tmeda)Pd(NO₃)₂] (M) with a tetradentate donor L¹ [benzene-1,4-di(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N,N,N′N′-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
Self-assembly of a cis-blocked Pd(II) 90 degrees ditopic acceptor [cis-(tmeda)Pd(NO3)(2)] (M) with a tetradentate donor L-1 [benzene-1,4-di(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N,N,N'N'-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed Spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 subset of MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
Self-assembly of a cis-blocked Pd­(II) 90° ditopic acceptor [cis-(tmeda)­Pd­(NO3)2] (M) with a tetradentate donor L 1 [benzene-1,4-di­(4-terpyridine)] in 2:1 molar ratio yielded two isometric molecular barrels MB1 and MB3 in DMSO [tmeda = N,N,N′N′-tetramethylethane-1,2-diamine]. Exclusive formation of the symmetrical tetrafacial barrel (MB1) was achieved when the self-assembly was performed in aqueous medium. The presence of a large confined cavity makes MB1 a potential molecular container. Spiropyran (SP) compounds exist in stable closed spiro form in visible light and convert to transient open merocyanine (MC) form upon irradiation with UV-light or upon strong heating. The transient MC form readily converts to the stable closed SP form in visible light. MB1 has been employed as a safe container to store the planar and unstable merocyanine isomers (MC1/2) of different spiropyran molecules (SP1/2) [SP1/2 = 6-bromo-spiropyran and 6-nitrospiropyran] for several days. The transient MC forms (MC1 and MC2) were found to be stable inside the molecular container MB1 under visible light and even in the presence of different stimuli such as heat and UV light for a long time. Such stabilization of MC forms inside the confined cavity of MB1 is noteworthy. This phenomenon was generalized by utilizing a carbazole-based molecular barrel (MB2) as a host, which also showed a similar stabilization of transient MC form in visible light at room temperature. Moreover, reverse thermochromism was observed as a result of heating of the MC1 ⊂ MB2 complex, which de-encapsulates the guest in the form of SP1 to give a colorless solution. Moreover, both the host molecules (MB1, MB2) were capable of stabilizing transient MC2 even in the solid state. Such stabilization of transient MC forms in the solid state and transformation of SP forms to MC forms in the solid state in the presence of molecular barrel are remarkable, and these properties have been employed in developing a magic ink.
Author Mondal, Bijnaneswar
Zangrando, Ennio
Purba, Prioti Choudhury
Howlader, Prodip
Mukherjee, Partha Sarathi
AuthorAffiliation Indian Institute of Science
Department of Chemical and Pharmaceutical Sciences
University of Trieste
Department of Inorganic and Physical Chemistry
AuthorAffiliation_xml – name: Department of Inorganic and Physical Chemistry
– name: University of Trieste
– name: Department of Chemical and Pharmaceutical Sciences
– name: Indian Institute of Science
Author_xml – sequence: 1
  givenname: Prodip
  orcidid: 0000-0001-6762-529X
  surname: Howlader
  fullname: Howlader, Prodip
  organization: Indian Institute of Science
– sequence: 2
  givenname: Bijnaneswar
  surname: Mondal
  fullname: Mondal, Bijnaneswar
  organization: Indian Institute of Science
– sequence: 3
  givenname: Prioti Choudhury
  surname: Purba
  fullname: Purba, Prioti Choudhury
  organization: Indian Institute of Science
– sequence: 4
  givenname: Ennio
  surname: Zangrando
  fullname: Zangrando, Ennio
  organization: University of Trieste
– sequence: 5
  givenname: Partha Sarathi
  orcidid: 0000-0001-6891-6697
  surname: Mukherjee
  fullname: Mukherjee, Partha Sarathi
  email: psm@ipc.iisc.ernet.in
  organization: Indian Institute of Science
BackLink https://www.ncbi.nlm.nih.gov/pubmed/29874066$$D View this record in MEDLINE/PubMed
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Snippet Self-assembly of a cis-blocked Pd­(II) 90° ditopic acceptor [cis-(tmeda)­Pd­(NO3)2] (M) with a tetradentate donor L 1 [benzene-1,4-di­(4-terpyridine)] in 2:1...
Self-assembly of a cis-blocked Pd(II) 90 degrees ditopic acceptor [cis-(tmeda)Pd(NO3)(2)] (M) with a tetradentate donor L-1 [benzene-1,4-di(4-terpyridine)] in...
Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [ cis-(tmeda)Pd(NO ) ] (M) with a tetradentate donor L [benzene-1,4-di(4-terpyridine)] in 2:1 molar...
Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [ cis-(tmeda)Pd(NO3)2] (M) with a tetradentate donor L1 [benzene-1,4-di(4-terpyridine)] in 2:1 molar...
Self-assembly of a cis-blocked Pd(II) 90° ditopic acceptor [cis-(tmeda)Pd(NO₃)₂] (M) with a tetradentate donor L¹ [benzene-1,4-di(4-terpyridine)] in 2:1 molar...
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SubjectTerms ambient temperature
Chemistry
Chemistry, Multidisciplinary
dimethyl sulfoxide
heat
irradiation
isomers
nitrates
Physical Sciences
Science & Technology
solids
ultraviolet radiation
Title Self-Assembled Pd(II) Barrels as Containers for Transient Merocyanine Form and Reverse Thermochromism of Spiropyran
URI http://dx.doi.org/10.1021/jacs.8b03946
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