Pub Date : 2022-01-02DOI: 10.1080/10610278.2023.2221365
Weerapat Foytong, Supak Pattaweepaiboon, Narongpol Kaewchangwat, Khomson Suttisintong, W. Sirisaksoontorn
ABSTRACT A novel spirooxazine, MeOBnSPO, as a fluorescence probe was successfully synthesised and its molecular structure was confirmed by single crystal X-ray crystallographic and spectroscopic analyses. The sensing performance of MeOBnSPO for Cu2+ was achieved with a ‘turn-on’ fluorescent detection in acetonitrile. The results demonstrated that MeOBnSPO possessed high selectivity towards Cu2+ with a 10-fold enhancement in fluorescence intensity (λem = 544 nm) and high sensitivity at the micromolar concentration. The limit of detection was calculated to be 19.1 nM. Evidence for the ring opening reaction and 1:1 stoichiometric complexation of MeOBnSPO to Cu2+ was proven by 1H NMR titration, FT-IR, MS, and Job analyses. Moreover, a drastic change in colour from colourless to bright yellow could provide naked-eye detection for Cu2+ with rapid response. The viable test strips of MeOBnSPO were also developed for Cu2+ colorimetric detection in mixed acetonitrile – H2O (50:50 v/v). GRAPHICAL ABSTRACT
{"title":"Synthesis, structural analysis and sensing performance of a novel spirooxazine derivative as a turn-on fluorescence probe for Cu2+ detection with high selectivity and sensitivity","authors":"Weerapat Foytong, Supak Pattaweepaiboon, Narongpol Kaewchangwat, Khomson Suttisintong, W. Sirisaksoontorn","doi":"10.1080/10610278.2023.2221365","DOIUrl":"https://doi.org/10.1080/10610278.2023.2221365","url":null,"abstract":"ABSTRACT A novel spirooxazine, MeOBnSPO, as a fluorescence probe was successfully synthesised and its molecular structure was confirmed by single crystal X-ray crystallographic and spectroscopic analyses. The sensing performance of MeOBnSPO for Cu2+ was achieved with a ‘turn-on’ fluorescent detection in acetonitrile. The results demonstrated that MeOBnSPO possessed high selectivity towards Cu2+ with a 10-fold enhancement in fluorescence intensity (λem = 544 nm) and high sensitivity at the micromolar concentration. The limit of detection was calculated to be 19.1 nM. Evidence for the ring opening reaction and 1:1 stoichiometric complexation of MeOBnSPO to Cu2+ was proven by 1H NMR titration, FT-IR, MS, and Job analyses. Moreover, a drastic change in colour from colourless to bright yellow could provide naked-eye detection for Cu2+ with rapid response. The viable test strips of MeOBnSPO were also developed for Cu2+ colorimetric detection in mixed acetonitrile – H2O (50:50 v/v). GRAPHICAL ABSTRACT","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"24 1","pages":"46 - 58"},"PeriodicalIF":3.3,"publicationDate":"2022-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85667554","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 : 2021-12-02DOI: 10.1080/10610278.2022.2161902
Andzelika Rutkauskaite, Lisa-Jane White, Jessica E. Boles, Kira Hilton, M. Clifford, B. Patenall, Bree R. Streather, Daniel P. Mulvihill, Samantha A. Henry, Mark Shepherd, J. Sutton, C. Hind, J. Hiscock
ABSTRACT Herein, we present the synthesis of two novel adamantane appended supramolecular self-associating amphiphiles. The antimicrobial efficacy of these compounds is determined against both clinically relevant Gram-positive methicillin-resistant Staphylococcus aureus and Gram-negative Escherichia coli. We also explore the self-associative properties of these amphiphiles in both polar organic DMSO-d 6 0.5% H2O and H2O (D2O)/EtOH 19:1 solutions, confirming aggregate stability through the determination of zeta potential values, aggregate size through a combination of 1H NMR DOSY and dynamic light scattering studies as appropriate, and critical aggregate concentration through the derivation of concentration-dependent surface tension values. We also perform a variety of 1H NMR dilution studies and in-silico modelling to further explore the roles of intermolecular hydrogen bonding and lipophilicity within aggregate formation and antimicrobial efficacy. Finally, we perform haemolysis and Galleria mellonella toxicity assays to establish the potential of these compounds to undergo further development as antibiotic agents. Graphical Abstract
{"title":"Adamantane appended antimicrobial supramolecular self-associating amphiphiles","authors":"Andzelika Rutkauskaite, Lisa-Jane White, Jessica E. Boles, Kira Hilton, M. Clifford, B. Patenall, Bree R. Streather, Daniel P. Mulvihill, Samantha A. Henry, Mark Shepherd, J. Sutton, C. Hind, J. Hiscock","doi":"10.1080/10610278.2022.2161902","DOIUrl":"https://doi.org/10.1080/10610278.2022.2161902","url":null,"abstract":"ABSTRACT Herein, we present the synthesis of two novel adamantane appended supramolecular self-associating amphiphiles. The antimicrobial efficacy of these compounds is determined against both clinically relevant Gram-positive methicillin-resistant Staphylococcus aureus and Gram-negative Escherichia coli. We also explore the self-associative properties of these amphiphiles in both polar organic DMSO-d 6 0.5% H2O and H2O (D2O)/EtOH 19:1 solutions, confirming aggregate stability through the determination of zeta potential values, aggregate size through a combination of 1H NMR DOSY and dynamic light scattering studies as appropriate, and critical aggregate concentration through the derivation of concentration-dependent surface tension values. We also perform a variety of 1H NMR dilution studies and in-silico modelling to further explore the roles of intermolecular hydrogen bonding and lipophilicity within aggregate formation and antimicrobial efficacy. Finally, we perform haemolysis and Galleria mellonella toxicity assays to establish the potential of these compounds to undergo further development as antibiotic agents. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"26 1","pages":"677 - 686"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81209799","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 : 2021-12-02DOI: 10.1080/10610278.2022.2163644
Chang-Zhi Li, E. Keene, Celymar Ortiz-de León, Leonard R. MacGillivray
ABSTRACT We report drug-drug cocrystals of the cytotoxic chemotherapy drugs 5-fluoro (5FU)/iodouracil (5IU) and the antiretroviral lamivudine (3TC). The cocrystal 2(5FU)·(3TC) is sustained by hydrogen bonds to generate a three-dimensional (3D) network while halogen bonds in the cocrystal (5IU)·(3TC) effectively disrupt hydrogen bonds to form layered assemblies. Graphical abstract
{"title":"Hydrogen and halogen bonds in drug-drug cocrystals of X-uracil (X = F, I) and lamivudine: extended quadruplex and layered assemblies","authors":"Chang-Zhi Li, E. Keene, Celymar Ortiz-de León, Leonard R. MacGillivray","doi":"10.1080/10610278.2022.2163644","DOIUrl":"https://doi.org/10.1080/10610278.2022.2163644","url":null,"abstract":"ABSTRACT We report drug-drug cocrystals of the cytotoxic chemotherapy drugs 5-fluoro (5FU)/iodouracil (5IU) and the antiretroviral lamivudine (3TC). The cocrystal 2(5FU)·(3TC) is sustained by hydrogen bonds to generate a three-dimensional (3D) network while halogen bonds in the cocrystal (5IU)·(3TC) effectively disrupt hydrogen bonds to form layered assemblies. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"10 1","pages":"687 - 692"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74404655","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 : 2021-12-02DOI: 10.1080/10610278.2023.2170233
Xiran Yang, Simin Liu
ABSTRACT Cucurbit[10]uril (CB[10]) is found to form stable host-guest complexes with tetracationic cyclophanes in H2O and DMSO. Upon encapsulation in CB[10], the affinity of cyclophanes towards anions is weakened, due to electronegative carbonyl oxygens on CB[10] providing charge repulsion environment, and encapsulation fixing the conformation of cyclophanes. Interestingly, these complexes show positively cooperative effects towards neutral phenol guests to form heteroternary complexes. The driving force for the formation of heteroternary inclusion complexes is multiple hydrogen bonding interactions confirmed by X-ray single crystal analysis, as well as hydrophobic effects. GRAPHICAL ABSTRACT
{"title":"Cationic cyclophanes-in-cucurbit[10]uril: host-in-host complexes showing cooperative recognition towards neutral phenol guests","authors":"Xiran Yang, Simin Liu","doi":"10.1080/10610278.2023.2170233","DOIUrl":"https://doi.org/10.1080/10610278.2023.2170233","url":null,"abstract":"ABSTRACT Cucurbit[10]uril (CB[10]) is found to form stable host-guest complexes with tetracationic cyclophanes in H2O and DMSO. Upon encapsulation in CB[10], the affinity of cyclophanes towards anions is weakened, due to electronegative carbonyl oxygens on CB[10] providing charge repulsion environment, and encapsulation fixing the conformation of cyclophanes. Interestingly, these complexes show positively cooperative effects towards neutral phenol guests to form heteroternary complexes. The driving force for the formation of heteroternary inclusion complexes is multiple hydrogen bonding interactions confirmed by X-ray single crystal analysis, as well as hydrophobic effects. GRAPHICAL ABSTRACT","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"75 1","pages":"693 - 700"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85559704","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 : 2021-12-02DOI: 10.1080/10610278.2022.2161901
K. Kravets, M. Kravets, Karolina Kędra, O. Danylyuk
ABSTRACT In this paper, we expand the utilisation of large and flexible macrocyclic host p-sulfonatocalix[8]arene (C8S) in building up solid state assemblies with both inorganic and organic cations. Upon coordination of sodium cations to all sulphonate groups of the macrocycle the 3-D coordination polymer is formed. The C8S adopts circular pleated loop conformation and macrocyclic molecules are assembled into stacks stapled by coordination to multiple sodium cations. The arrangement of the metallo-supramolecular assembly is pseudo-hexagonal. In the presence of organic cation berberine, the host-guest complex is favoured. Macrocycle adopts conformation without a substantial internal cavity with two of the benzenesulfonate groups being inclined towards the centre of the molecule. One host binds eight berberine guests in the grooves and clefts of the molecular surface of the macrocycle. C8S is a suitable host for berberine in the solid state, and such crystallisation-driven host-guest complexation has potential in expanding the library of berberine crystal forms. Graphical abstract
{"title":"P-Sulfonatocalix[8]arene coordinates sodium cations and forms host-guest complex with berberine: insight from crystal structure","authors":"K. Kravets, M. Kravets, Karolina Kędra, O. Danylyuk","doi":"10.1080/10610278.2022.2161901","DOIUrl":"https://doi.org/10.1080/10610278.2022.2161901","url":null,"abstract":"ABSTRACT In this paper, we expand the utilisation of large and flexible macrocyclic host p-sulfonatocalix[8]arene (C8S) in building up solid state assemblies with both inorganic and organic cations. Upon coordination of sodium cations to all sulphonate groups of the macrocycle the 3-D coordination polymer is formed. The C8S adopts circular pleated loop conformation and macrocyclic molecules are assembled into stacks stapled by coordination to multiple sodium cations. The arrangement of the metallo-supramolecular assembly is pseudo-hexagonal. In the presence of organic cation berberine, the host-guest complex is favoured. Macrocycle adopts conformation without a substantial internal cavity with two of the benzenesulfonate groups being inclined towards the centre of the molecule. One host binds eight berberine guests in the grooves and clefts of the molecular surface of the macrocycle. C8S is a suitable host for berberine in the solid state, and such crystallisation-driven host-guest complexation has potential in expanding the library of berberine crystal forms. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"14 1","pages":"666 - 676"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75608624","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 : 2021-12-02DOI: 10.1080/10610278.2023.2175678
Yufen Sun, Fan Wu, Hu Gao, Xu Zhi, Yue Zhao, Zhenrong Shen
ABSTRACT Here, we report the facile synthesis of Cu(II) tetraaryl-tetranaphtoporphyrin CuTNP showing an extremely sharp, intense Q band above 700 nm via retro-Diels-Alder approach. The highly saddled structure of CuTNP was confirmed using X-ray single-crystal diffraction. The optical and magnetic properties of CuTNP, as well as its excellent reversible redox behaviours, were thoroughly examined both experimentally and theoretically. The water-soluble nanocomposites encapsulating CuTNP by bent amphiphilic molecules were successfully developed, which kept the intense Q band of CuTNP in water. The strong photoacoustic response of CuTNP was detected, suggesting its potential as a photoacoustic imaging agent. This work provides metal-coordinated linearly π-extended porphyrins as potential functional materials for future biomedical applications. Graphical abstract
{"title":"Copper naphthoporphyrin showing enhanced water-solubility by nano-encapsulation and efficient photoacoustic response","authors":"Yufen Sun, Fan Wu, Hu Gao, Xu Zhi, Yue Zhao, Zhenrong Shen","doi":"10.1080/10610278.2023.2175678","DOIUrl":"https://doi.org/10.1080/10610278.2023.2175678","url":null,"abstract":"ABSTRACT Here, we report the facile synthesis of Cu(II) tetraaryl-tetranaphtoporphyrin CuTNP showing an extremely sharp, intense Q band above 700 nm via retro-Diels-Alder approach. The highly saddled structure of CuTNP was confirmed using X-ray single-crystal diffraction. The optical and magnetic properties of CuTNP, as well as its excellent reversible redox behaviours, were thoroughly examined both experimentally and theoretically. The water-soluble nanocomposites encapsulating CuTNP by bent amphiphilic molecules were successfully developed, which kept the intense Q band of CuTNP in water. The strong photoacoustic response of CuTNP was detected, suggesting its potential as a photoacoustic imaging agent. This work provides metal-coordinated linearly π-extended porphyrins as potential functional materials for future biomedical applications. Graphical abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"14 1","pages":"717 - 724"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90823823","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}
ABSTRACT Efficient detection of trace water was important before use in water-sensitive reactions. Herein, a fluorescence sensor 1,4-bis((E)-(2-(benzo[d]thiazol-2-yl)hydrazineylidene)methyl)benzene (DHB) was designed and synthesised by a simple one-step reaction using 2-hydrazinobenzothiazole and terephthalaldehyde as raw materials. DHB showed aggregation-induced emission characteristics in solid state and 1,4-dioxane/H2O mixture. In addition, the fluorescent colour changes in IPA and fluorescence quenching in N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), dimethyl sulphoxide (DMSO), glycerine (GI), and 1,3-propanediol (1,3-PDO) were obviously observed with increasing water content, making DHB a highly sensitive fluorescent sensor for water detection with a detection limit of 0.174% for IPA, 0.040% for DMSO, 0.067% for DMF, 0.039% for DMA, 0.069% for 1,3-PDO, and 0.013% for GI, respectively. Further, DHB displayed fluorescence colorimetric response to water in solid state. 1H NMR titration indicated that the sensing mechanism for the detection of trace water was form hydrogen bonds between H2O molecule and amino group of DHB. Graphical Abstract: A highly sensitive fluorescent probe DHB with AIE characteristics for water detection with a detection limit of 0.174% for IPA, 0.040% for DMSO, 0.067% for DMF, 0.039% for DMA, 0.069% for 1,3-PDO and 0.013% for GI. Further, DHB displayed fluorescence colorimetric response to Al3+ in solid state
{"title":"Fluorescence probe with AIE properties for ratiometric/turn off detecting of water in organic solvents and solid state","authors":"Na Li, Yong-E Gao, Qian Zhang, Jianming Gu, Zhi-Ying Li, Junliang Yang, Yan-Dong Liu, Xingming Zhang, Wei Wen","doi":"10.1080/10610278.2023.2173073","DOIUrl":"https://doi.org/10.1080/10610278.2023.2173073","url":null,"abstract":"ABSTRACT Efficient detection of trace water was important before use in water-sensitive reactions. Herein, a fluorescence sensor 1,4-bis((E)-(2-(benzo[d]thiazol-2-yl)hydrazineylidene)methyl)benzene (DHB) was designed and synthesised by a simple one-step reaction using 2-hydrazinobenzothiazole and terephthalaldehyde as raw materials. DHB showed aggregation-induced emission characteristics in solid state and 1,4-dioxane/H2O mixture. In addition, the fluorescent colour changes in IPA and fluorescence quenching in N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), dimethyl sulphoxide (DMSO), glycerine (GI), and 1,3-propanediol (1,3-PDO) were obviously observed with increasing water content, making DHB a highly sensitive fluorescent sensor for water detection with a detection limit of 0.174% for IPA, 0.040% for DMSO, 0.067% for DMF, 0.039% for DMA, 0.069% for 1,3-PDO, and 0.013% for GI, respectively. Further, DHB displayed fluorescence colorimetric response to water in solid state. 1H NMR titration indicated that the sensing mechanism for the detection of trace water was form hydrogen bonds between H2O molecule and amino group of DHB. Graphical Abstract: A highly sensitive fluorescent probe DHB with AIE characteristics for water detection with a detection limit of 0.174% for IPA, 0.040% for DMSO, 0.067% for DMF, 0.039% for DMA, 0.069% for 1,3-PDO and 0.013% for GI. Further, DHB displayed fluorescence colorimetric response to Al3+ in solid state","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"67 1","pages":"709 - 716"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76523725","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 : 2021-12-02DOI: 10.1080/10610278.2023.2173072
S. Jothinayaki, Ravindhiran Ramya, Sankar Srividhya, J. Kiruthika, Krishnamurthy Ramya, Sivarajan Karthiga, M. Arunachalam, Dhandapani Kavitha
ABSTRACT Host–guest complexation of decamethoxypillar[5]arene and difunctionalized pillar[4]arene[1]quinone with isatin were demonstrated by 1H NMR titration experiments. The antibacterial potentials of isatin, decamethoxypillar[5]arene, difunctionalized pillar[4]arene[1]quinone and their isatin inclusion complexes were evaluated against both Gram-positive and Gram-negative bacteria by the well-diffusion method. The results of the antibacterial assay revealed that decamethoxypillar[5]arene displayed very good antibacterial activity than the difunctionalized pillar[4]arene[1]quinone. Isatin inclusion complex of decamethoxypillar[5]arene showed very good antibacterial activity as that of chloramphenicol with S. aureus, P. aeruginosa, K. pneumoniae and E. coli. Checkerboard assay revealed synergic effects of P[5]A and isatin combinations against selected microorganisms. In silico toxicity predictions suggested the potential of isatin, decamethoxypillar[5]arene and the difunctionalized pillar[4]arene[1]quinone as prospective drug candidates. Graphical abstract Isatin inclusion complex of decamethoxy pillar[5]arene showed very good antibacterial activity as that of chloramphenicol with S. aureus, P. aeruginosa, K. pneumoniae and E. coli.
{"title":"Antibacterial potentials of pillar[5]arene, pillar[4]arene[1]quinone derivative and their isatin inclusion complexes","authors":"S. Jothinayaki, Ravindhiran Ramya, Sankar Srividhya, J. Kiruthika, Krishnamurthy Ramya, Sivarajan Karthiga, M. Arunachalam, Dhandapani Kavitha","doi":"10.1080/10610278.2023.2173072","DOIUrl":"https://doi.org/10.1080/10610278.2023.2173072","url":null,"abstract":"ABSTRACT Host–guest complexation of decamethoxypillar[5]arene and difunctionalized pillar[4]arene[1]quinone with isatin were demonstrated by 1H NMR titration experiments. The antibacterial potentials of isatin, decamethoxypillar[5]arene, difunctionalized pillar[4]arene[1]quinone and their isatin inclusion complexes were evaluated against both Gram-positive and Gram-negative bacteria by the well-diffusion method. The results of the antibacterial assay revealed that decamethoxypillar[5]arene displayed very good antibacterial activity than the difunctionalized pillar[4]arene[1]quinone. Isatin inclusion complex of decamethoxypillar[5]arene showed very good antibacterial activity as that of chloramphenicol with S. aureus, P. aeruginosa, K. pneumoniae and E. coli. Checkerboard assay revealed synergic effects of P[5]A and isatin combinations against selected microorganisms. In silico toxicity predictions suggested the potential of isatin, decamethoxypillar[5]arene and the difunctionalized pillar[4]arene[1]quinone as prospective drug candidates. Graphical abstract Isatin inclusion complex of decamethoxy pillar[5]arene showed very good antibacterial activity as that of chloramphenicol with S. aureus, P. aeruginosa, K. pneumoniae and E. coli.","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"106 1","pages":"701 - 708"},"PeriodicalIF":3.3,"publicationDate":"2021-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87962531","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 : 2021-11-02DOI: 10.1080/10610278.2022.2142122
Lu Yang, Cui-Yin Nie, Ying Han, Jun Ye, Wenlong Liu, Chaoguo Yan
ABSTRACT A series of the functionalised pillar[5]arene ureidopyrimidinone derivatives were successfully synthesised by the condensation reaction of mono-amido-functionalised pillar[5]arenes with 2-(1-Imidazolylcarbonylamino)-6-methyl-4-pyrimidinone in dry chloroform. 1H NMR, 2D NOESY spectra and single crystal structure clearly indicated that novel [1]rotaxanes were formed by insertion of longer alkylene chain into the cavities of the pillar[5]arenes. On the other hand, the ureidopyrimidinone-functionalised pillar[5]arenes tend to form the dimer in chloroform and in solid state through the self-complementary quadruple hydrogen bonding of the ureidopyrimidinone. GRAPHICAL ABSTRACT
{"title":"Construction and crystal structures of pillar[5]arene-based bis-[1]rotaxanes via quadruple hydrogen bonding of ureidopyrimidinone","authors":"Lu Yang, Cui-Yin Nie, Ying Han, Jun Ye, Wenlong Liu, Chaoguo Yan","doi":"10.1080/10610278.2022.2142122","DOIUrl":"https://doi.org/10.1080/10610278.2022.2142122","url":null,"abstract":"ABSTRACT A series of the functionalised pillar[5]arene ureidopyrimidinone derivatives were successfully synthesised by the condensation reaction of mono-amido-functionalised pillar[5]arenes with 2-(1-Imidazolylcarbonylamino)-6-methyl-4-pyrimidinone in dry chloroform. 1H NMR, 2D NOESY spectra and single crystal structure clearly indicated that novel [1]rotaxanes were formed by insertion of longer alkylene chain into the cavities of the pillar[5]arenes. On the other hand, the ureidopyrimidinone-functionalised pillar[5]arenes tend to form the dimer in chloroform and in solid state through the self-complementary quadruple hydrogen bonding of the ureidopyrimidinone. GRAPHICAL ABSTRACT","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"34 1","pages":"625 - 633"},"PeriodicalIF":3.3,"publicationDate":"2021-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82334856","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 : 2021-11-02DOI: 10.1080/10610278.2022.2151366
M. Panneerselvam, M. Deepan Kumar, Prasannan Nisanth, M. Jaccob, R. Vijay Solomon
ABSTRACT Based on density functional theory calculations, we have addressed the electronic structure, binding and nature of non-covalent interactions between alkylated pillar[5]arene (P[5]A) and 1,4-dicyanobutane (DCB)-based host-guest macrocycles. Neutral 1,4-dicyanobutane-based alkylated DCB_ProP[5]A is found to show higher binding energy when compared to the other three host-guest macrocycles. These complexes are largely stabilised by non-covalent interactions, which are ascertained through NCI and QTAIM analyses. Furthermore, the second-order perturbation energy of NBO analysis show that LP (N) – σ*(C-H) interactions predominate in DCB_ProP[5]A complex. Particularly, alkyl substituents (-methyl, -ethyl and -propyl) are playing a vital role in stabilising the host-guest complexes. In summary, the present work not only exhibits an efficient strategy to build a new family of alkylated P[5]A inclusion complexes but also providing deeper understanding on various non-covalent interactions towards 1,4-dicyanobutane (DCB) guest molecules inside the host environment. Graphical Abstract
{"title":"Quantum mechanical study on complexation phenomenon of pillar[5]arene towards neutral dicyanobutane","authors":"M. Panneerselvam, M. Deepan Kumar, Prasannan Nisanth, M. Jaccob, R. Vijay Solomon","doi":"10.1080/10610278.2022.2151366","DOIUrl":"https://doi.org/10.1080/10610278.2022.2151366","url":null,"abstract":"ABSTRACT Based on density functional theory calculations, we have addressed the electronic structure, binding and nature of non-covalent interactions between alkylated pillar[5]arene (P[5]A) and 1,4-dicyanobutane (DCB)-based host-guest macrocycles. Neutral 1,4-dicyanobutane-based alkylated DCB_ProP[5]A is found to show higher binding energy when compared to the other three host-guest macrocycles. These complexes are largely stabilised by non-covalent interactions, which are ascertained through NCI and QTAIM analyses. Furthermore, the second-order perturbation energy of NBO analysis show that LP (N) – σ*(C-H) interactions predominate in DCB_ProP[5]A complex. Particularly, alkyl substituents (-methyl, -ethyl and -propyl) are playing a vital role in stabilising the host-guest complexes. In summary, the present work not only exhibits an efficient strategy to build a new family of alkylated P[5]A inclusion complexes but also providing deeper understanding on various non-covalent interactions towards 1,4-dicyanobutane (DCB) guest molecules inside the host environment. Graphical Abstract","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"197 1","pages":"634 - 646"},"PeriodicalIF":3.3,"publicationDate":"2021-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75920776","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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