Pub Date : 2023-06-28DOI: 10.1142/s1088424623501110
Jorge Labella, J. García-Calvo, M. Ramírez-Como, J. Pallarès, L. Marsal, T. Torres
{"title":"Perylenemonoimide-subphthalocyanine derivatives: Synthesis, characterization and photovoltaic performance as non-fullerene acceptors in bulk heterojunction solar cells","authors":"Jorge Labella, J. García-Calvo, M. Ramírez-Como, J. Pallarès, L. Marsal, T. Torres","doi":"10.1142/s1088424623501110","DOIUrl":"https://doi.org/10.1142/s1088424623501110","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48683521","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 : 2023-06-28DOI: 10.1142/s1088424623501158
W. R. Osterloh, T. Chilingaryan, B. Habermeyer, C. Frochot, P. Arnoux, R. Guilard, K. Kadish
{"title":"Electrochemistry of tri-N-methylpyridyl porphyrins","authors":"W. R. Osterloh, T. Chilingaryan, B. Habermeyer, C. Frochot, P. Arnoux, R. Guilard, K. Kadish","doi":"10.1142/s1088424623501158","DOIUrl":"https://doi.org/10.1142/s1088424623501158","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44050229","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 : 2023-06-27DOI: 10.1142/s1088424623501006
Rohan Bhimpuria, Kiran Reddy Baddigam, F. Xu, J. Wells, K. Borbas
Three free-base and two Zn(II) porphyrins carrying one alkene-substituted meso-aryl group and three solubilizing pentyl groups were prepared via mixed aldehyde-type syntheses. A meso [Formula: see text]-allyloxyphenyl porphyrin was obtained via the corresponding 5-([Formula: see text]-allyloxyphenyl) dipyrromethane. The porphyrins were fully characterized using a combination of NMR spectroscopy, high-resolution mass spectrometry, and UV-Vis absorption and emission spectroscopies. Two of the free-base porphyrins were heated in the presence of AIBN or benzoyl peroxide as the initiator. The major isolated products of these reactions contained two porphyrin units based on the results of MALDI-MS and 1H NMR analysis data, which was supported by the results of FTIR, UV-Vis absorption and emission spectroscopies, and gel permeation and liquid chromatographies. Additionally, the acrylamide-functionalized porphyrin could be attached to a polylysine scaffold under basic conditions. These results suggest that the olefinic handle can be used to assemble structures containing multiple porphyrinic macrocycles.
{"title":"Synthesis of styrene, phenyl acrylate and allyloxyphenyl-functionalized porphyrins, and preliminary exploration of their utility for assembling multiple porphyrin units","authors":"Rohan Bhimpuria, Kiran Reddy Baddigam, F. Xu, J. Wells, K. Borbas","doi":"10.1142/s1088424623501006","DOIUrl":"https://doi.org/10.1142/s1088424623501006","url":null,"abstract":"Three free-base and two Zn(II) porphyrins carrying one alkene-substituted meso-aryl group and three solubilizing pentyl groups were prepared via mixed aldehyde-type syntheses. A meso [Formula: see text]-allyloxyphenyl porphyrin was obtained via the corresponding 5-([Formula: see text]-allyloxyphenyl) dipyrromethane. The porphyrins were fully characterized using a combination of NMR spectroscopy, high-resolution mass spectrometry, and UV-Vis absorption and emission spectroscopies. Two of the free-base porphyrins were heated in the presence of AIBN or benzoyl peroxide as the initiator. The major isolated products of these reactions contained two porphyrin units based on the results of MALDI-MS and 1H NMR analysis data, which was supported by the results of FTIR, UV-Vis absorption and emission spectroscopies, and gel permeation and liquid chromatographies. Additionally, the acrylamide-functionalized porphyrin could be attached to a polylysine scaffold under basic conditions. These results suggest that the olefinic handle can be used to assemble structures containing multiple porphyrinic macrocycles.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46331218","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 : 2023-06-19DOI: 10.1142/s1088424623300112
P. Harvey
{"title":"Removal of heavy and toxic metals from wastewater using porphyrin-based covalent-organic frameworks: An emerging Field","authors":"P. Harvey","doi":"10.1142/s1088424623300112","DOIUrl":"https://doi.org/10.1142/s1088424623300112","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46813850","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 : 2023-06-19DOI: 10.1142/s1088424623501080
H. Bak, P. Cavigli, A. Bond, Theis Brock‐Nannestad, M. Pittelkow, E. Iengo
{"title":"Sn(IV)-corroles reversibly bind carboxylates in the axial position","authors":"H. Bak, P. Cavigli, A. Bond, Theis Brock‐Nannestad, M. Pittelkow, E. Iengo","doi":"10.1142/s1088424623501080","DOIUrl":"https://doi.org/10.1142/s1088424623501080","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44805409","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 : 2023-06-19DOI: 10.1142/s1088424623500566
F. Bolze
During the pandemic period, we were forced to reconsider teaching of practical labs, as students had mainly to work at home. It was the occasion to explore the use of cheap microcontroller kits for teaching chemistry and to work out some manipulations with household products. Back to normal life, it is important to valorize this equipment and work to design simple chemistry experiments which could be performed by students at home with Arduino kits adapted to chemistry, to illustrate various courses in addition to classical manipulations performed in the laboratory with specific equipment and products. We describe here the construction of a simple and cheap Arduino-based fluorimeter and its use to study relative porphyrinoids (mainly chlorophylls and pheophytins) contents in olive oils, and the effect of heating on the degradation of such substances. We used an Arduino Uno kit with a LED, a light-to-frequency converter associated with an excitation-blocking filter, and a 3D-printed sample holder.
{"title":"Teaching with Arduino: Porphyrinoids’ fluorescence in olive oil","authors":"F. Bolze","doi":"10.1142/s1088424623500566","DOIUrl":"https://doi.org/10.1142/s1088424623500566","url":null,"abstract":"During the pandemic period, we were forced to reconsider teaching of practical labs, as students had mainly to work at home. It was the occasion to explore the use of cheap microcontroller kits for teaching chemistry and to work out some manipulations with household products. Back to normal life, it is important to valorize this equipment and work to design simple chemistry experiments which could be performed by students at home with Arduino kits adapted to chemistry, to illustrate various courses in addition to classical manipulations performed in the laboratory with specific equipment and products. We describe here the construction of a simple and cheap Arduino-based fluorimeter and its use to study relative porphyrinoids (mainly chlorophylls and pheophytins) contents in olive oils, and the effect of heating on the degradation of such substances. We used an Arduino Uno kit with a LED, a light-to-frequency converter associated with an excitation-blocking filter, and a 3D-printed sample holder.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41550636","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 : 2023-06-19DOI: 10.1142/s1088424623500918
Frederico F. Martins, M. Swart
Here we study the effect of metals on the characteristic Soret band of N-confused porphyrins. We used DFT calculations to study how this low-lying region of the spectrum of the NCP-2H isomer is affected by the introduction of transition metals with various ([Formula: see text], [Formula: see text], [Formula: see text] and [Formula: see text] d-electron configurations. The spin ground state of these complexes is mostly dependent on the number of unpaired electrons, both with and without the presence of an axial ligand. The analysis of the electronic distribution and spin density showed that these unpaired electrons are often harbored by the N-confused porphyrin ring instead of on the metal. Time-dependent DFT results indicated that the aromatic system of porphyrin is disrupted in the N-confused isomer: instead of the typical large Soret band, this now gives rise to two peaks of much lower intensity. Most metallo-porphyrins exhibited similar optical properties, with the HOMO/LUMO orbitals showing a mixed metal/porphyrin character. The only exception was the Rh metalloporphyrin that exhibited a ligand-to-metal charge transfer band with increasing intensity as function of the ligand field. This suggests Rh is the only metal whose orbitals are higher in energy than the ligand’s, indicating that it is the only system where the redox processes occur on the metal.
{"title":"Electronic properties and redox chemistry of N-confused metalloporphyrins","authors":"Frederico F. Martins, M. Swart","doi":"10.1142/s1088424623500918","DOIUrl":"https://doi.org/10.1142/s1088424623500918","url":null,"abstract":"Here we study the effect of metals on the characteristic Soret band of N-confused porphyrins. We used DFT calculations to study how this low-lying region of the spectrum of the NCP-2H isomer is affected by the introduction of transition metals with various ([Formula: see text], [Formula: see text], [Formula: see text] and [Formula: see text] d-electron configurations. The spin ground state of these complexes is mostly dependent on the number of unpaired electrons, both with and without the presence of an axial ligand. The analysis of the electronic distribution and spin density showed that these unpaired electrons are often harbored by the N-confused porphyrin ring instead of on the metal. Time-dependent DFT results indicated that the aromatic system of porphyrin is disrupted in the N-confused isomer: instead of the typical large Soret band, this now gives rise to two peaks of much lower intensity. Most metallo-porphyrins exhibited similar optical properties, with the HOMO/LUMO orbitals showing a mixed metal/porphyrin character. The only exception was the Rh metalloporphyrin that exhibited a ligand-to-metal charge transfer band with increasing intensity as function of the ligand field. This suggests Rh is the only metal whose orbitals are higher in energy than the ligand’s, indicating that it is the only system where the redox processes occur on the metal.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44059580","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 : 2023-06-12DOI: 10.1142/s1088424623501067
M. Shire Sudi, Long Zhao, Yuqin Dou, Xin Yang, Qi Wang, Aijian Wang, Wei Zhu
{"title":"Enhanced photoelectrochemical water oxidation of a BiVO4/tetra(amino)phthalocyanine composite photoanode","authors":"M. Shire Sudi, Long Zhao, Yuqin Dou, Xin Yang, Qi Wang, Aijian Wang, Wei Zhu","doi":"10.1142/s1088424623501067","DOIUrl":"https://doi.org/10.1142/s1088424623501067","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48182903","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 : 2023-06-01DOI: 10.1142/s1088424623300100
Benard M. Isaiah, Edith K Amuhaya, Clare I. Muhanji
The fight against pathogenic microorganisms has in recent decades been met with fierce setbacks owing to the antimicrobial resistance phenomenon. Conventional antimicrobials have thus weakened in their effectiveness against microbes, calling for the development of innovative strategies to combat the emerging global health crisis. A promising therapy for filling this gap is photodynamic antimicrobial chemotherapy which destroys microorganisms by making use of the combined action of a photosensitizer, light, and oxygen. The modality inactivates a wide range of pathogens, including bacteria, fungi, protozoa, and viruses. Of greater interest in photodynamic antimicrobial chemotherapy is the ability to destroy resistant strains of microbes without encouraging selection for resistance genes, thus immensely contributing to the fight against antimicrobial resistance. Different PSs vary in their microbial inactivation efficacies. Therefore, various structural modification approaches are being adopted to improve their respective activities. In this paper, recent studies focusing on strategies employed to improve the effectiveness and efficacies of PSs used in photodynamic antimicrobial chemotherapy are reviewed.
{"title":"Advances in efficacy enhancement of photosensitizer-mediated photodynamic antimicrobial chemotherapy","authors":"Benard M. Isaiah, Edith K Amuhaya, Clare I. Muhanji","doi":"10.1142/s1088424623300100","DOIUrl":"https://doi.org/10.1142/s1088424623300100","url":null,"abstract":"The fight against pathogenic microorganisms has in recent decades been met with fierce setbacks owing to the antimicrobial resistance phenomenon. Conventional antimicrobials have thus weakened in their effectiveness against microbes, calling for the development of innovative strategies to combat the emerging global health crisis. A promising therapy for filling this gap is photodynamic antimicrobial chemotherapy which destroys microorganisms by making use of the combined action of a photosensitizer, light, and oxygen. The modality inactivates a wide range of pathogens, including bacteria, fungi, protozoa, and viruses. Of greater interest in photodynamic antimicrobial chemotherapy is the ability to destroy resistant strains of microbes without encouraging selection for resistance genes, thus immensely contributing to the fight against antimicrobial resistance. Different PSs vary in their microbial inactivation efficacies. Therefore, various structural modification approaches are being adopted to improve their respective activities. In this paper, recent studies focusing on strategies employed to improve the effectiveness and efficacies of PSs used in photodynamic antimicrobial chemotherapy are reviewed.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41578506","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 : 2023-05-31DOI: 10.1142/s108842462350058x
Jaehwan Sim, Meng Li, K. Park, K. Kim
Visualization of mitochondria with cyanine dyes has been exploited to study the functions of mitochondria. However, proteins interacting with cyanine dyes have not been investigated clearly. Here, we report a chemical proteomics approach for the identification of mitochondrial proteins associated with cyanine dyes. This approach uses affinity-based photocrosslinking of Cy5-diazirine-alkyne (Cy5-DAyne) in combination with selective enrichment of target proteins by bio-orthogonal supramolecular latching based on unique host-guest interaction between cucurbit[7]uril (CB[7]) and its selected guest such as adamantylammonium (AdA). The enriched proteins then were analyzed using LC–MS/MS to provide a list of proteins closely associated with the Cy5 motif. This study suggests that the proteomic environment around the Cy5 motif is highly associated with energy production processes, including the respiratory chain, ATP synthesis, and fatty acid oxidization. Moreover, it demonstrates the potential of this chemical proteomic approach for the investigation of other organellar proteins using different selective dyes.
{"title":"Identification of mitochondrial proteins associated with cyanine 5 using a combination of affinity-based photocrosslinking with bio-orthogonal supramolecular latching","authors":"Jaehwan Sim, Meng Li, K. Park, K. Kim","doi":"10.1142/s108842462350058x","DOIUrl":"https://doi.org/10.1142/s108842462350058x","url":null,"abstract":"Visualization of mitochondria with cyanine dyes has been exploited to study the functions of mitochondria. However, proteins interacting with cyanine dyes have not been investigated clearly. Here, we report a chemical proteomics approach for the identification of mitochondrial proteins associated with cyanine dyes. This approach uses affinity-based photocrosslinking of Cy5-diazirine-alkyne (Cy5-DAyne) in combination with selective enrichment of target proteins by bio-orthogonal supramolecular latching based on unique host-guest interaction between cucurbit[7]uril (CB[7]) and its selected guest such as adamantylammonium (AdA). The enriched proteins then were analyzed using LC–MS/MS to provide a list of proteins closely associated with the Cy5 motif. This study suggests that the proteomic environment around the Cy5 motif is highly associated with energy production processes, including the respiratory chain, ATP synthesis, and fatty acid oxidization. Moreover, it demonstrates the potential of this chemical proteomic approach for the investigation of other organellar proteins using different selective dyes.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42798152","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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