Pub Date : 2023-03-06DOI: 10.1142/s1088424623500633
Ilia A. Dereven’kov, Ilya I. Dzvinkas, V. S. Osokin, S. Makarov
{"title":"Effect of bovine serum albumin on the water solubility of hydrophobic corrinoids","authors":"Ilia A. Dereven’kov, Ilya I. Dzvinkas, V. S. Osokin, S. Makarov","doi":"10.1142/s1088424623500633","DOIUrl":"https://doi.org/10.1142/s1088424623500633","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47514675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-06DOI: 10.1142/s1088424623500712
Yuki Takarada, Nobuyuki Hara, S. Ogasawara, H. Tamiaki
{"title":"Synthesis of 31-aminopyridinio–chlorophyll-a derivatives and their optical properties","authors":"Yuki Takarada, Nobuyuki Hara, S. Ogasawara, H. Tamiaki","doi":"10.1142/s1088424623500712","DOIUrl":"https://doi.org/10.1142/s1088424623500712","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47468787","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-06DOI: 10.1142/s1088424623500694
Kyosuke Yamagata, Oscar Fernandez-Vera, S. Seki, Takayuki Tanaka
{"title":"Phenylboron(III) complexes of tripyrrins: A new class of macrocycles closed by hydrogen-bonding","authors":"Kyosuke Yamagata, Oscar Fernandez-Vera, S. Seki, Takayuki Tanaka","doi":"10.1142/s1088424623500694","DOIUrl":"https://doi.org/10.1142/s1088424623500694","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44202592","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-06DOI: 10.1142/s1088424623500670
Dustin E. Nevonen, Jacob W. Schaffner, P. Hanrahan, M. Shepit, J. van Lierop, D. Blank, V. Nemykin
{"title":"Crystal structure, stability, spectroscopy, electronic structure, and ultrafast excited-state dynamics of the elusive iron(II) phthalocyanine axially coordinated with DABCO ligands","authors":"Dustin E. Nevonen, Jacob W. Schaffner, P. Hanrahan, M. Shepit, J. van Lierop, D. Blank, V. Nemykin","doi":"10.1142/s1088424623500670","DOIUrl":"https://doi.org/10.1142/s1088424623500670","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44123972","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-06DOI: 10.1142/s1088424623500669
S. Makarov, S. Ketkov, I. Grishin, D. Wohrle
{"title":"Synthesis of heterometallic binuclear cobalt(II) phthalocyanines and their catalytic activity in the oxidation of a mercaptan","authors":"S. Makarov, S. Ketkov, I. Grishin, D. Wohrle","doi":"10.1142/s1088424623500669","DOIUrl":"https://doi.org/10.1142/s1088424623500669","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44145210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-06DOI: 10.1142/s1088424623500657
E. Tracy, Penny Joshi, M. Dukh, F. Durrani, R. Pandey, H. Baumann
{"title":"Galactosyl, alkyl, and acidic groups modify uptake and subcellular deposition of pyropheophorbide-a by epithelial tumor cells and determine photosensitizing efficacy","authors":"E. Tracy, Penny Joshi, M. Dukh, F. Durrani, R. Pandey, H. Baumann","doi":"10.1142/s1088424623500657","DOIUrl":"https://doi.org/10.1142/s1088424623500657","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42413341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-03-03DOI: 10.1142/s1088424623500219
Phuong-Lien Doan Cao, Zhiyuan Wu, J. Rong, J. Lindsey
Tetrapyrrole building blocks are invaluable constituents in the construction of molecular architectures for use in biomimicry, functional materials, and biomedicine. The reaction of dipyrromethane and the triisopropylsilyl-protected 3,5-diethynylbenzaldehyde afforded the corresponding trans-A2-porphyrin (free base) bearing four ethynes. Subsequent meso-bromination, Suzuki coupling, and protecting group removal afforded a porphyrin building block bearing four ethynes and one benzylamine. The reaction of dipyrromethane and 3,5-bis(propargyloxy)benzaldehyde afforded the corresponding trans-A2-porphyrin (free base) bearing four ethynes. The reaction of 5-(3,5-bis(propargyloxy)phenyl)dipyrromethane and the Eschenmoser (1,9-dimethylaminomethyl) derivative of a 5-([Formula: see text]-substituted aryl)dipyrromethane was used to create two trans-AB-porphyrins (zinc chelates). The [Formula: see text]-substituent of the aryl group was cyano or an acetal moiety. Hydrolysis of the acetal and a click reaction with m-PEG24-azide gave the bis(PEGylated)porphyrin-carboxaldehyde. The porphyrins present readily derivatizable functional groups in a compact architecture.
{"title":"Porphyrin building blocks bearing two or four divergent ethynes","authors":"Phuong-Lien Doan Cao, Zhiyuan Wu, J. Rong, J. Lindsey","doi":"10.1142/s1088424623500219","DOIUrl":"https://doi.org/10.1142/s1088424623500219","url":null,"abstract":"Tetrapyrrole building blocks are invaluable constituents in the construction of molecular architectures for use in biomimicry, functional materials, and biomedicine. The reaction of dipyrromethane and the triisopropylsilyl-protected 3,5-diethynylbenzaldehyde afforded the corresponding trans-A2-porphyrin (free base) bearing four ethynes. Subsequent meso-bromination, Suzuki coupling, and protecting group removal afforded a porphyrin building block bearing four ethynes and one benzylamine. The reaction of dipyrromethane and 3,5-bis(propargyloxy)benzaldehyde afforded the corresponding trans-A2-porphyrin (free base) bearing four ethynes. The reaction of 5-(3,5-bis(propargyloxy)phenyl)dipyrromethane and the Eschenmoser (1,9-dimethylaminomethyl) derivative of a 5-([Formula: see text]-substituted aryl)dipyrromethane was used to create two trans-AB-porphyrins (zinc chelates). The [Formula: see text]-substituent of the aryl group was cyano or an acetal moiety. Hydrolysis of the acetal and a click reaction with m-PEG24-azide gave the bis(PEGylated)porphyrin-carboxaldehyde. The porphyrins present readily derivatizable functional groups in a compact architecture.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44546544","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-02-27DOI: 10.1142/s1088424623500141
Declan McKearney, Wen Zhou, Myles Scollon, Taniyuki Furuyama, V. Williams, D. Leznoff
The addition of ether functional groups to a metallophthalocyanine ring is known to significantly decrease the oxidation potentials of the ring. In this light, the impact of the branching of alkyl-ether groups on the electronic properties was investigated via the synthesis of non-peripheral ([Formula: see text]-substituted n-butyl (1), iso-butyl (2) and sec-butyl (3) 1,4,8,11,15,18,22,25-octabutoxyphthalocyanines, in conjunction with Co and Cu metal centers. From 1 to 3 the first and second ring-based oxidation potentials were decreased by 70 mV and 110 mV respectively both for Cu and Co-containing complexes; the UV-visible Q-band maxima only changed by 4-8 nm, consistent with the destabilization of both the HOMO and LUMO, as confirmed by TD-DFT calculations. The reversibility of both redox couples was improved via branching (3) for the Co complexes. All six complexes were structurally characterized, with varying levels and types of ring distortions. All molecules show 1-D supramolecular stacking, but for n-butoxy 1Co an intermolecular Co-O interaction aligns the molecular stacks, while for sec-butoxy 3Co only [Formula: see text]-[Formula: see text] stacking of the Pc-ring was present. Both 3Co and 3Cu were ring-oxidized at lower potentials than 1Co and 1Cu, and the increased steric bulk from the branched ether chains prevented the overlap of their N8C8 inner rings.
{"title":"Decreasing the aggregation and ligand redox potential of metallophthalocyanines through branched ether functionalization","authors":"Declan McKearney, Wen Zhou, Myles Scollon, Taniyuki Furuyama, V. Williams, D. Leznoff","doi":"10.1142/s1088424623500141","DOIUrl":"https://doi.org/10.1142/s1088424623500141","url":null,"abstract":"The addition of ether functional groups to a metallophthalocyanine ring is known to significantly decrease the oxidation potentials of the ring. In this light, the impact of the branching of alkyl-ether groups on the electronic properties was investigated via the synthesis of non-peripheral ([Formula: see text]-substituted n-butyl (1), iso-butyl (2) and sec-butyl (3) 1,4,8,11,15,18,22,25-octabutoxyphthalocyanines, in conjunction with Co and Cu metal centers. From 1 to 3 the first and second ring-based oxidation potentials were decreased by 70 mV and 110 mV respectively both for Cu and Co-containing complexes; the UV-visible Q-band maxima only changed by 4-8 nm, consistent with the destabilization of both the HOMO and LUMO, as confirmed by TD-DFT calculations. The reversibility of both redox couples was improved via branching (3) for the Co complexes. All six complexes were structurally characterized, with varying levels and types of ring distortions. All molecules show 1-D supramolecular stacking, but for n-butoxy 1Co an intermolecular Co-O interaction aligns the molecular stacks, while for sec-butoxy 3Co only [Formula: see text]-[Formula: see text] stacking of the Pc-ring was present. Both 3Co and 3Cu were ring-oxidized at lower potentials than 1Co and 1Cu, and the increased steric bulk from the branched ether chains prevented the overlap of their N8C8 inner rings.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49217103","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-02-18DOI: 10.1142/s1088424623500608
Jan Herritsch, Malte Zugermeier, M. Schmid, Min Chen, Jan-Niclas Luy, Peter Schweyen, Martin Broring, R. Tonner-Zech, J. Michael Gottfried
{"title":"Why can cobalt(III) corrole form more stable metal/organic interfaces than cobalt(II) porphyrin?","authors":"Jan Herritsch, Malte Zugermeier, M. Schmid, Min Chen, Jan-Niclas Luy, Peter Schweyen, Martin Broring, R. Tonner-Zech, J. Michael Gottfried","doi":"10.1142/s1088424623500608","DOIUrl":"https://doi.org/10.1142/s1088424623500608","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43164990","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-02-18DOI: 10.1142/s108842462350061x
Calvin V Chau, Martin R. Johnson, Daniel N Mangel, J. Sessler
{"title":"Synthesis and characterization of an expanded antiaromatic macrocycle porphyrin analogue","authors":"Calvin V Chau, Martin R. Johnson, Daniel N Mangel, J. Sessler","doi":"10.1142/s108842462350061x","DOIUrl":"https://doi.org/10.1142/s108842462350061x","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47596342","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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