Journal of Porphyrins and Phthalocyanines最新文献

{"title":"A BODIPY-Hoechst conjugate for nuclear DNA staining.","authors":"Amit Kumar Singh, Andrea Tomassini, Giulio Palummieri, Diana Velluto, Françisco M Raymo","doi":"10.1142/s1088424625501068","DOIUrl":"10.1142/s1088424625501068","url":null,"abstract":"<p><p>Hoechst dyes bind noncovalently to DNA with a significant fluorescence enhancement. As a result, they are routinely used to stain the cell nucleus in diverse fluorescence imaging and flow cytometry applications. The short wavelengths necessary for their excitation, however, cause autofluorescence and photodamage. To overcome these limitations, we envisaged the possibility of integrating a borondipyrromethene (BODIPY) chromophore and a Hoechst ligand in the same molecular construct. Here, we report the synthesis of this BODIPY-Hoechst conjugate and demonstrate that the covalent connection of the two components has minimal influence on the photophysical properties of one and the binding ability of the other. Indeed, our compound binds to nuclear DNA, enabling cell imaging under excitation with green light from the BODIPY chromophore and the detection of its intense fluorescence.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"29 10-11","pages":"1177-1183"},"PeriodicalIF":1.0,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12915998/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146226957","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Al-TCPP MOF Coated flake-μAl <i>via in situ</i> growth: A chloride-resistant energetic material","authors":"Xinyue Hu, Lele Tong, Jia Xu, Runxiang Tan, Jieqian Liu, Jian Mao","doi":"10.1142/s1088424625500749","DOIUrl":"https://doi.org/10.1142/s1088424625500749","url":null,"abstract":"Aluminum powders are widely recognized for their exceptional energy density and combustion performance, making them indispensable in applications such as solid propellants, explosives, and pyrotechnics. However, their performance is significantly reduced by chloride-induced corrosion when mixed with perchlorate-based oxidizers. To address this issue, we developed a coating layer of Al-TCPP nanosheets on the surface of flake micro-aluminum (flake-[Formula: see text] Al) powder using an in situ growth technique, resulting in a flake-[Formula: see text] Al@Al-TCPP composite. Compared to uncoated flake-[Formula: see text] Al, the Al-TCPP coating exhibits remarkable Cl[Formula: see text] corrosion resistance, with no phase or morphological degradation observed even after 65 days in a 3.5 wt% NaCl solution. This improvement is attributed to the ability of the Al-TCPP shell’s ability to generate singlet oxygen ( 1 O[Formula: see text] and hydroxyl radicals (⋅OH), which facilitates the self-repair of the oxide film following chloride-induced pitting. Furthermore, the combustion calorific value of the coated product retains up to 92% of that of flake micro-aluminum powder, with only a 2.85% loss in combustion calorific value after soaking in a 3.5 wt% NaCl solution for 10 days. Our findings offer a novel approach to aluminum-based energetic materials, providing unparalleled stability and performance.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"29 09","pages":"974-980"},"PeriodicalIF":0.0,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147906889","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}

{"title":"Effect of ligands on heme dimethyl ester-based hexa-coordinated complexes as oxygen-carrying carriers","authors":"Baojuan Zhao, Yiman Lan, Xiaodan Wang, Yan Ma, Run-Meng Li, Wei Cao, Xiang Wang","doi":"10.1142/s1088424624500627","DOIUrl":"https://doi.org/10.1142/s1088424624500627","url":null,"abstract":"Most of the previous artificial oxygen carriers realized the oxygen-carrying function through a reversible combination of penta-coordinated iron(II) porphyrin with oxygen. The other oxygen transport model, in which oxygen competes with other ligands for binding with central ions, has been rarely studied. In this study, oxygen-carrying properties of a series of hexa-coordinated complexes were investigated, with heme dimethyl ester working as an oxygen-carrying component. In addition, both oxygen uptake and the auto-oxidation rate of the hexa-coordinated complexes were also explored. The results indicate that the hexa-coordinated complexes can effectively carry oxygen, provided that there is at least one strong ligand on the fifth or sixth coordination site of the heme dimethyl ester. Promisingly, when one ligand is strong and the other ligand is weak, the hexa-coordinated complexes can exhibit highly efficient oxygen-carrying capacity. By fixing weak ligands and changing strong ligands, it was found that the coordination ability of strong ligands has a significant impact on the oxygenation curve of the system. Furthermore, the auto-oxidation rate of the hexa-coordinated complexes of heme dimethyl ester is related to the hydrophobicity of the fifth and sixth ligands. The longer the hydrophobic chain of the ligand, the slower the auto-oxidation rate. Consequently, the oxygen-binding mode of this heme derivative has the potential to be an effective oxygen carrier.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"28 11n12","pages":"798-805"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147904677","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}

{"title":"N-Alkylcorroles","authors":"Francesco Pizzoli, Sara Nardis, Alessia Fata, Martina Marsotto, Greta Petrella, Frank R. Fronczek, Kevin M. Smith, Roberto Paolesse","doi":"10.1142/s1088424624500196","DOIUrl":"https://doi.org/10.1142/s1088424624500196","url":null,"abstract":"<p>A series of inner core <span><math altimg=\"eq-00001.gif\" display=\"inline\" overflow=\"scroll\"><mi>N</mi></math></span><span></span>-alkylcorroles were synthesized and characterized. The introduction of both linear and branched alkyl groups was achieved, demonstrating the quite large scope of the reaction. Polyalkylation results in the formation of the <span><math altimg=\"eq-00002.gif\" display=\"inline\" overflow=\"scroll\"><mi>N</mi></math></span><span></span>-21,<span><math altimg=\"eq-00003.gif\" display=\"inline\" overflow=\"scroll\"><mi>N</mi></math></span><span></span>-22 regioisomer, although the introduction of the second alkyl group is less facile than previously observed in the case of the methyl substituent. Complete functionalization of the inner core nitrogens has been investigated, but only the N,N<span><math altimg=\"eq-00004.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mi>′</mi></mrow></msup></math></span><span></span>,N<span><math altimg=\"eq-00005.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mi>′′</mi></mrow></msup></math></span><span></span>-trimethyl derivatives were obtained. The characterization of these species demonstrated a different arrangement of the methyl groups to the macrocyclic plane, which is peculiar when compared with the conformation of the analogous porphyrin derivatives. These <span><math altimg=\"eq-00006.gif\" display=\"inline\" overflow=\"scroll\"><mi>N</mi></math></span><span></span>-alkylcorroles should prove to be of potential interest as ligands for various metal ions.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"28 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884525","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}

{"title":"Study of six coordinated cobalt(III) oxophlorin with different axial ligands: Optimization of geometry and determining of energy and electronic configuration at various spin states by employing of B3LYP, BV86P and M06-2X methods","authors":"Homayoon Bahrami, Narges Ostadhosseini, Hamid Reza Shamlouei, Mansour Zahedi","doi":"10.1142/s1088424624500147","DOIUrl":"https://doi.org/10.1142/s1088424624500147","url":null,"abstract":"<p>The six coordinated Co^IIIoxophlorin have been studied with imidazole, pyridine and t-butylcyanide as axial ligands using B3LYP, BV86P and MO6-2X methods. Conversion between two isomers [(L)₂Co^III(PO)]<span><math altimg=\"eq-00001.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mo stretchy=\"false\">†</mo></mrow></msup></math></span><span></span> and [(L)₂Co^III(PO)]<span><math altimg=\"eq-00002.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mo>|</mo><mo>|</mo></mrow></msup></math></span><span></span> can be occurred at various spin multiplicities, namely singlet, triplet and quintet states. L is employed to show axial ligand namely, imidazole or pyridine. London forces have a basic role in the stability of the mentioned complexes due to non-specific solvent effects. The latter fact has been obtained using the PCM model. Also, it is specified that minimum geometries have not been obtained for some parallel or perpendicular six-coordinated complexes with special axial ligands at a finite spin state. The B3LYP method indicates that one and three <span><math altimg=\"eq-00003.gif\" display=\"inline\" overflow=\"scroll\"><mi>α</mi></math></span><span></span>-electron can be found on the Co atom in every optimized complex at triplet and quintet spin states, respectively. Also, another <span><math altimg=\"eq-00004.gif\" display=\"inline\" overflow=\"scroll\"><mi>α</mi></math></span><span></span>-electron is placed on the ring of oxophlorin. This fact is obtained for different isomers of [(IM₂(Co^III(PO)] and [(Py)₂Co^III(PO)] at triplet and quintet spin states, while these complexes are optimized using B3LYP. Besides, results obtained from B3LYP show that the most stable state for six coordinated Co^IIIoxophlorin with any axial ligand is the singlet state. Based on crystal field theory and molecular orbital theory, electron configuration and hybridization of cobalt in [(IM)₂Co^III(PO)] at singlet state can be written as t₂g⁶ eg⁰ and sp³d², respectively. Former electronic configuration indicates a strong field with low spin for d orbitals of cobalt, and latter hybridization is expected for a metal with a coordination number of 6 in a complex with O_h symmetry. The results obtained are completely satisfied by NBO analysis.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"160 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140802972","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}

{"title":"A novel 5,10,15,20-tetrakis-(4-(triazol-1-yl)phenyl)porphyridine compound: Crystal structure, photophysical properties and TDDFT calculations","authors":"Hao-Dong Liu, Xi-Yu Shao, Long-Hua Zeng, Yu-Yue Xu, Cheng Liu, Sheng-Ping Dai, Chang-Wang Pan, Wen-Tong Chen","doi":"10.1142/s108842462450010x","DOIUrl":"https://doi.org/10.1142/s108842462450010x","url":null,"abstract":"<p>A novel 5,10,15,20-tetrakis-(4-(triazol-1-yl)phenyl)porphyridine compound, namely, Zn[5,10,15,20-tetrakis-(4-(triazol-1-yl)phenyl)porphyridine] (hereafter tagged as <b>1</b>) was synthesized through a solvothermal reaction with mixed solvents at 413 K. The X-ray single-crystal structure of compound <b>1</b> is featured as a two-dimensional (2D) layer-like structure with the zinc ion located at the center of the 5,10,15,20-tetrakis-(4-(triazol-1-yl)phenyl)porphyridine. The macrocycle of the 5,10,15,20-tetrakis-(4-(triazol-1-yl)phenyl)porphyridine is coplanar. The zinc ion has six coordination and coordinates with three porphyridines. The photoluminescence spectra of compound <b>1</b> with DMF solution reveal that it shows upconversion red photoluminescence. The time-dependent density functional theory (TDDFT) calculation confirms that this upconversion red photoluminescence originated from the MLCT process (metal to ligand charge transfer). The CCT (Correlated Color Temperature) is 2200 K and the CIE (Commission Internationale de I’Éclairage) chromaticity coordinate is (0.6311, 0.3595) for compound <b>1</b>. The UV-vis diffuse reflectance curve measured with a solid state sample reveals that compound <b>1</b> possesses a 2.75 eV band gap.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"14 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140598456","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}

{"title":"An “on-off-on” fluorescent sensor based on TSPP-gallic acid: Visual detection of S2− in actual samples","authors":"Yuanyuan Liu, Tianfeng Ma, Jing Li, Lin Shi, Xiaohua Xu, Huan Wang","doi":"10.1142/s1088424624500068","DOIUrl":"https://doi.org/10.1142/s1088424624500068","url":null,"abstract":"<p>A novel “on-off-on” switches fluorescence sensor based on TSPP-gallic acid (GA) for S<span><math altimg=\"eq-00002.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mn>2</mn><mo stretchy=\"false\">−</mo></mrow></msup></math></span><span></span>-detecting was designed in this article. 5,10,15,20- (4-sulphonatophenyl) porphyrin (TSPP) was synthesized by a modified “one-pot” method. The synthesized TSPP was used as a fluorescence probe for the construction of a fluorescence sensing system. At room temperature, the maximum fluorescence emission wavelength could be obtained at 642 nm when the excitation wavelength was 515 nm when the fluorescence signal was in the “on” mode. The TSPP solution appeared pink in color at this moment. When GA was introduced into the TSPP solution, the fluorescence signal was turned off (fluorescence intensity was quenched) due to the protonation of TSPP, which was caused by the weak acidity of GA. The color of the TSPP solution changed from pink to green. Following that, an acid-base reaction between S<span><math altimg=\"eq-00003.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mn>2</mn><mo stretchy=\"false\">−</mo></mrow></msup></math></span><span></span>and GA was initiated when S<span><math altimg=\"eq-00004.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mn>2</mn><mo stretchy=\"false\">−</mo></mrow></msup></math></span><span></span>was introduced into the TSPP-GA system, leading to the liberation of TSPP and restoration of fluorescence intensity. The solution color reverted to red, indicating that the fluorescence sensing system had returned to the “on” mode. The TSPP-GA system had good selectivity and sensitivity to S<span><math altimg=\"eq-00005.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mn>2</mn><mo stretchy=\"false\">−</mo></mrow></msup></math></span><span></span>, the linear range was 4.52 × 10<span><math altimg=\"eq-00006.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mo stretchy=\"false\">−</mo><mn>6</mn></mrow></msup></math></span><span></span> M <span><math altimg=\"eq-00007.gif\" display=\"inline\" overflow=\"scroll\"><mo>∼</mo></math></span><span></span> 4.34 × 10<span><math altimg=\"eq-00008.gif\" display=\"inline\" overflow=\"scroll\"><msup><mrow></mrow><mrow><mo stretchy=\"false\">−</mo><mn>4</mn></mrow></msup></math></span><span></span> M, and the detection limit (LOD) was 0.87 <span><math altimg=\"eq-00009.gif\" display=\"inline\" overflow=\"scroll\"><mi>μ</mi></math></span><span></span>M. It could be used to detect sulfur ions in actual samples with satisfactory recoveries and RSD values.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"1 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140299338","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}

{"title":"Solvatochromism of a saddle-distorted cationic Zn(II)-porphyrin complex","authors":"Hidemi Ochiai, Tomoya Ishizuka, Hiro Tanaka, Yoshihito Shiota, Kazunari Yoshizawa, Takahiko Kojima","doi":"10.1142/s108842462450007x","DOIUrl":"https://doi.org/10.1142/s108842462450007x","url":null,"abstract":"<p>A saddle-distorted and cationic Zn(II)-porphyrin complex was revealed to exhibit solvatochromism in organic solvents, depending on the donor numbers. The color change was derived from the alteration of the HOMO-LUMO gap caused by the distortion of the porphyrin mean plane due to solvent coordination.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"119 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140303374","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}

{"title":"Porphyrins as key components for photoinduced charge separation, solar cells, and optogenetics","authors":"Hiroshi Imahori, Midori Akiyama","doi":"10.1142/s1088424624300015","DOIUrl":"https://doi.org/10.1142/s1088424624300015","url":null,"abstract":"<p>This review presents typical examples of porphyrins, which serve as highly effective building blocks, primarily drawn from our past achievements. They function as both an electron donor and an energy donor/acceptor in various applications. These applications include photosynthetic and solar cell models, dye-sensitized solar cells, bulk heterojunction solar cells, and optogenetics based on photoinduced charge separation. Consequently, porphyrins are essential components for evaluating energy and electron transfer properties, as well as for energy and biological applications.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"6 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140200001","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}

{"title":"Optical sensor properties of a novel BODIPY compound for non-enzymatic detection of glucose","authors":"Selma K. Yıldırım, İpek Ömeroğlu, Mahmut Durmuş","doi":"10.1142/s1088424624500056","DOIUrl":"https://doi.org/10.1142/s1088424624500056","url":null,"abstract":"<p>This work demonstrated the preparation and characterization of a novel 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivative containing boronic acid group and investigation of its non-invasive/non-enzymatic fluorescence sensor behavior for determination of glucose. The novel BODIPY derivative bearing boronic acid pinacol ester (<b>BODIPY-1</b>) was synthesized by Sonogashira coupling reaction between <b>Iodo-BODIPY</b> and 4-ethynylphenylboronic acid pinacol ester. The target novel <b>BODIPY-2</b> compound which was used as a fluorescence probe for the determination of glucose was synthesized from <b>BODIPY-1</b> by changing the pinacol ester group to the boric acid moieties. The fluorescence intensity of the <b>BODIPY-2</b> fluorophore decreased when it interacted with the glucose. Sensing performance towards to glucose of this probe was evaluated in detail concerning the suitable solvent, linear concentration range, convenient pH, limit of detection (LOD), limit of quantification (LOQ) and selectivity. The LOD value of <b>BODIPY-2</b> was found 0.19 mM toward glucose. Also, the complex stoichiometry between the <b>BODIPY-2</b> and glucose molecules was determined by Job’s plot technique.</p>","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"4 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140200073","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}