Study on the Photoluminescent and Thermal Properties of Zinc Complexes with a N6O4 Macrocyclic Ligand
Abstract
:1. Introduction
2. Results and Discussion
2.1. Elucidation of the Structures of the Compounds
2.2. TG-DTA Properties of the Complexes
2.3. Photoluminescent Properties
3. Materials and Methods
3.1. Instrumentation and Reagents
3.2. Synthesis of L0
3.3. Synthesis of L1
3.4. General Synthetic Procedure for the Preparation of Zinc Compounds (Scheme 1)
3.4.1. [Zn2L1 (DMSO)4](OSO2CF3)4 (1)
3.4.2. [Zn2(p-OSO2PhCH3)4L1] (2)
3.4.3. [Zn2(OCOCH3)4L1] (3)
3.4.4. [Zn2(OCOPh)4L1] (4)
3.4.5. [Zn2(o-OCOPhOH)4L1] (5)
3.4.6. [Zn2(m-OCOPhOH)4L1] (6)
3.4.7. [Zn2(p-OCOPhOH)4L1] (7)
3.5. Crystal Structure Determinations
3.6. Photoluminescent Property Measurement
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
- Amouri, H.; Desmarets, C.; Moussa, J. Confined nanospaces in metallocages: Guest molecules, weakly encapsulated anions, and catalyst sequestration. Chem. Rev. 2012, 112, 2015–2041. [Google Scholar] [CrossRef] [PubMed]
- Alibrandi, G.; Arena, C.G.; Lando, G.; Vecchio, C.L.; Parisi, M.F. {[1.1.1]Cryptand/Imidazole}: A prototype composite kinetic molecular device for automatic NMR variable pH reaction monitoring. Chem.-Eur. J. 2011, 17, 1419–1422. [Google Scholar] [CrossRef] [PubMed]
- Garcia, J.; Kuda-Wedagedara, A.N.W.; Allen, M.J. Physical properties of Eu2+-Containing cryptates as contrast agents for ultrahigh-field magnetic resonance imaging. Eur. J. Inorg. Chem. 2012, 2012, 2135–2140. [Google Scholar] [CrossRef] [PubMed]
- Nelson, J.; Mckee, V.; Morgan, G. Coordination chemistry of azacryptands. Prog. Inorg. Chem. 1998, 47, 167–316. [Google Scholar] [CrossRef]
- Geoghegan, P.; O’Leary, P. Hydroxyamide-based ligands and their use in the asymmetric catalysis of key organic transformations. ACS Catal. 2012, 2, 573–591. [Google Scholar] [CrossRef]
- Mateus, P.; Delgado, R.; Brandao, P.; Felix, V. Dicarboxylate recognition by two macrobicyclic receptors: Selectivity for fumarate over maleate. J. Org. Chem. 2012, 77, 4611–4621. [Google Scholar] [CrossRef] [PubMed]
- Zhu, K.-L.; Wu, L.; Yan, X.-Z.; Zheng, B.; Zhang, M.-M.; Huang, F.-H. Anion-assisted complexation of paraquat by cryptands based on bis(m-phenylene)-[32]crown-10. Chem.-Eur. J. 2010, 16, 6088–6098. [Google Scholar] [CrossRef] [PubMed]
- Alibrandi, G.; Lo Vecchio, C.; Lando, G. [1.1.1]Cryptand: A molecular automatic titrator. Angew. Chem.-Int. Ed. 2009, 48, 6332–6334. [Google Scholar] [CrossRef] [PubMed]
- Xu, Z.-K.; Huang, X.-M.; Liang, J.-D.; Zhang, S.-H.; Zhou, S.-G.; Chen, M.-J.; Tang, M.-F.; Jiang, L.-S. Efficient syntheses of novel cryptands based on bis(m-phenylene)-26-crown-8 and their complexation with paraquat. Eur. J. Org. Chem. 2010, 10, 1904–1911. [Google Scholar] [CrossRef]
- Gamage, N.D.H.; Mei, Y.J.; Garcia, J.; Allen, M.J. Oxidatively stable, aqueous europium(II) complexes through steric and electronic manipulation of cryptand coordination chemistry. Chem.-Int. Ed. 2010, 49, 8923–8925. [Google Scholar] [CrossRef] [PubMed]
- Chaloner, L.; Askari, M.S.; Kutteh, A.; Schindler, S.; Ottenwaelder, X. Formation and reactivity of a biomimetic hydroperoxocopper(II) cryptate. Eur. J. Inorg. Chem. 2011, 27, 4204–4211. [Google Scholar] [CrossRef]
- Liu, M.; Li, S.J.; Hu, M.L.; Wang, F.; Huang, F.H. Selectivity algorithm for the formation of two cryptand/paraquat catenanes. Org. Lett. 2010, 12, 760–763. [Google Scholar] [CrossRef] [PubMed]
- Hao, H.G.; Zheng, X.D.; Lu, T.B. Photoinduced catalytic reaction by a fluorescent active cryptand containing an anthracene fragment. Angew. Chem.-Int. Ed. 2010, 49, 8148–8151. [Google Scholar] [CrossRef] [PubMed]
- Alliger, G.E.; Muller, P.; Do, L.H.; Cummins, C.C.; Nocera, D.G. Family of cofacial bimetallic complexes of a hexaanionic carboxamide cryptand. Inorg. Chem. 2011, 50, 4107–4115. [Google Scholar] [CrossRef] [PubMed]
- Cangelosi, V.M.; Carter, T.G.; Crossland, J.L.; Zakharov, L.N.; Johnson, D.W. Self-assembled E2L3 cryptands (E = P, As, Sb, Bi): Transmetalation, Homo-and Heterometallic assemblies, and conformational isomerism. Inorg. Chem. 2010, 49, 9985–9992. [Google Scholar] [CrossRef] [PubMed]
- Yan, X.-Z.; Wei, P.-F.; Zhang, M.-M.; Chi, X.-D.; Liu, J.-Y.; Huang, F.-H. Pseudorotaxanes based on the recognition of cryptands to vinylogous viologens. Org. Lett. 2011, 13, 6370–6373. [Google Scholar] [CrossRef] [PubMed]
- Ma, Z.; Shi, H.-D.; Deng, X.-Q.; da Silva, M.F.C.G.; Martins, L.M.D.R.S.; Pombeiro, A.J.L. Silver coordination polymers with tri- and hexacyanoethyl-functionalized macrocyclic ligands. Dalton Trans. 2015, 44, 1388–1396. [Google Scholar] [CrossRef] [PubMed]
- Saeed, M.A.; Wong, B.M.; Fronczek, F.R.; Venkatraman, R.; Hossain, M.A. Formation of an amine-water cyclic pentamer: A new type of water cluster in a polyazacryptand. Cryst. Growth Des. 2010, 10, 1486–1488. [Google Scholar] [CrossRef] [PubMed]
- Liu, M.; Yan, X.-Z.; Hu, M.-L.; Chen, X.-P.; Zhang, M.-M.; Zheng, B.; Hu, X.-H.; Shao, S.; Huang, F.-H. Photoresponsive host-guest systems based on a new azobenzene-containing crytpand. Org. Lett. 2010, 12, 2558–2561. [Google Scholar] [CrossRef]
- Alliger, G.E.; Muller, P.; Cummins, C.C.; Nocera, D.G. Cofacial dicobalt complex of a binucleating hexacarboxamide cryptand ligand. Inorg. Chem. 2010, 49, 3697–3699. [Google Scholar] [CrossRef] [PubMed]
- Bischof, C.; Wahsner, J.; Scholten, J.; Trosien, S.; Seitz, M. Quantification of C-H quenching in near-IR luminescent ytterbium and neodymium cryptates. J. Am. Chem. Soc. 2010, 132, 14334–14335. [Google Scholar] [CrossRef] [PubMed]
- Cangelosi, V.M.; Zakharov, L.N.; Johnson, D.W. Supramolecular “Transmetalation” leads to an unusual self-assembled P2L3 cryptand. Angew. Chem.-Int. Ed. 2010, 49, 1248–1251. [Google Scholar] [CrossRef] [PubMed]
- Yoshida, A.; Nakagawa, Y.; Uehara, K.; Hikichi, S.; Mizuno, N. Inorganic cryptand: Size-selective strong metallic cation encapsulation by a disilicoicosatungstate (Si2W20) polyoxometalate. Angew. Chem.-Int. Ed. 2009, 48, 7055–7058. [Google Scholar] [CrossRef] [PubMed]
- Shen, Z.-L.; Jordan, R.F. Self-assembled tetranuclear palladium catalysts that produce high molecular weight linear polyethylene. J. Am. Chem. Soc. 2010, 132, 52–53. [Google Scholar] [CrossRef] [PubMed]
- Mateus, P.; Delgado, R.; Brandao, P.; Felix, V. Recognition of oxalate by a copper(II) polyaza macrobicyclic complex. Chem.-Eur. J. 2011, 17, 7020–7031. [Google Scholar] [CrossRef] [PubMed]
- Hossain, M.A.; Saeed, M.A.; Fronczek, F.R.; Wong, B.M.; Dey, K.R.; Mendy, J.S.; Gibson, D. Charge-assisted encapsulation of two chlorides by a hexaprotonated azamacrocycle. Cryst. Growth Des. 2010, 10, 1478–1481. [Google Scholar] [CrossRef] [PubMed]
- Semenov, V.E.; Giniyatullin, R.K.; Mikhailov, A.S.; Nikolaev, A.E.; Kharlamov, S.V.; Latypov, S.K.; Reznik, V.S. Unusual reaction of macrocyclic uracils with paraformaldehyde. Eur. J. Org. Chem. 2011, 28, 5423–5426. [Google Scholar] [CrossRef]
- Felton, C.E.; Harding, L.P.; Jones, J.E.; Kariuki, B.M.; Pope, S.J.A.; Rice, C.R. A wavelength and lifetime responsive cryptate-containing fluorescent probe for zinc ions in water. Chem. Commun. 2008, 46, 6185–6187. [Google Scholar] [CrossRef] [PubMed]
- Alzakhem, N.; Bischof, C.; Seitz, M. Dependence of the photophysical properties on the number of 2,2′-bipyridine units in a series of luminescent europium and terbium cryptates. Inorg. Chem. 2012, 51, 9343–9349. [Google Scholar] [CrossRef] [PubMed]
- Brietzke, T.; Mickler, W.; Kelling, A.; Schilde, U.; Kruger, H.J.; Holdt, H.J. Mono- and dinuclear ruthenium(II)-1,6,7,12-tetraazaperylene complexes of N,N’-dimethyl-2,1 1-diaza[3.3](2,6)-pyridinophane. Eur. J. Inorg. Chem. 2012, 29, 4632–4643. [Google Scholar] [CrossRef]
- Bazzicalupi, C.; Bencini, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B. Lead complexation by novel phenanthroline-containing macrocycles. J. Chem. Soc. Dalton Trans. 1999, 3, 393–399. [Google Scholar] [CrossRef]
- Bazzicalupi, C.; Bencini, A.; Biagini, S.; Bianchi, A.; Faggi, E.; Giorgi, C.; Marchetta, M.; Totti, F.; Valtancoli, B. Polyamine receptors containing dipyridine or phenanthroline units: Clues for the design of fluorescent chemosensors for metal ions. Chem.-Eur. J. 2009, 15, 8049–8063. [Google Scholar] [CrossRef] [PubMed]
- Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Giorgi, C.; Fusi, V.; Valtancoli, B.; Bernardo, M.A.; Pina, F. Effect of protonation and Zn(II) coordination on the fluorescence emission of a phenanthroline-containing macrocycle. An unusual case of “nonemissive” Zn(II) complex. Inorg. Chem. 1999, 38, 3806–3813. [Google Scholar] [CrossRef]
- Caron, A.; Guilhelm, J.; Riche, C.; Pascard, C.; Alpha, B.; Lehn, J.M.; Rodriguez-Ubis, J.C. Photoactive cryptands. Crystal structure of the sodium cryptate of the tris(phenanthroline) macrobicyclic ligand. Helv. Chim. Acta 1985, 68, 1577–1582. [Google Scholar] [CrossRef]
- Petoud, S.; Cohen, S.M.; Bunzli, J.C.G.; Raymond, K.N. Stable lanthanide luminescence agents highly emissive in aqueous solution: Multidentate 2-hydroxyisophthalamide complexes of SM3+, Eu3+, Tb3+, Dy3+. J. Am. Chem. Soc. 2003, 125, 13324–13325. [Google Scholar] [CrossRef] [PubMed]
- Xu, J.D.; Corneillie, T.M.; Moore, E.G.; Law, G.L.; Butlin, N.G.; Raymond, K.N. Octadentate cages of Tb(III) 2-hydroxyisophthalamides: A new standard for luminescent lanthanide labels. J. Am. Chem. Soc. 2011, 133, 19900–19910. [Google Scholar] [CrossRef] [PubMed]
- Chen, Q.Y.; Luo, Q.H.; Hu, X.L.; Shen, M.C.; Chen, J.T. Heterodinuclear cryptates [EuML(dmf)](ClO4)(2) (M = Ca, Cd, Ni, Zn): Tuning the luminescence of europium(III) through the selection of the second metal ion. Chem.-Eur. J. 2002, 8, 3984–3990. [Google Scholar] [CrossRef]
- Ma, Z.; Lu, W.-B.; Liang, B.-H.; Pombeiro, A.J.L. Synthesis, characterization, photoluminescent and thermal properties of zinc(II) 4′-phenyl-terpyridine compounds. New J. Chem. 2013, 37, 1529–1537. [Google Scholar] [CrossRef]
- Ma, Z.; Cao, Y.-Q.; Li, Q.-S.; da Silva, M.F.C.G.; da Silva, J.J.R.F.; Pombeiro, A.J.L. Synthesis, characterization, solid-state photo-luminescence and anti-tumor activity of zinc(II) 4′-phenyl-terpyridine compounds. J. Inorg. Biochem. 2010, 104, 704–711. [Google Scholar] [CrossRef] [PubMed]
- Hamann, C.; Kern, J.M.; Sauvage, J.P. Zinc(II)-templated synthesis of a [2]-catenane 2,2′,6′,2″-terpyridine-incorporating cycle and a 1,10-phenanthroline-containing ring. Inorg. Chem. 2003, 42, 1877–1883. [Google Scholar] [CrossRef] [PubMed]
- Ma, Z.; Liu, S.-X. Synthesis and characterization of a 42-membered macrocyclic compound C40H46N6O4 with [2+2] condensation. Chin. J. Struct. Chem. 2003, 22, 553–557. [Google Scholar]
- Bruker, APEX2 & SAINT; Bruker, AXS Inc.: Madison, WI, USA, 2004.
- Agilent, CrysAlis PRO; Agilent Technologies: Yarnton, England, UK, 2012.
- Sheldrick, G.M. Phase annealing in SHELX-90: Direct methods for larger structures. Acta Crystallogr. Sect. A 1990, 46, 467–473. [Google Scholar] [CrossRef]
- Sheldrick, G.M. A short history of SHELX. Acta Crystallogr. Sect. A 2008, 64, 112–122. [Google Scholar] [CrossRef] [PubMed]
- Farrugia, L.J. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 1999, 32, 837–838. [Google Scholar] [CrossRef]
- Williams, A.T.R.; Winfield, S.A.; Miller, J.N. Relative fluorescence quantum yields using a computer controlled luminescence spectrometer. Analyst 1983, 108, 1067–1071. [Google Scholar] [CrossRef]
- Suzuki, K.; Kobayashi, A.; Kaneko, S.; Takehira, K.; Yoshihara, T.; Ishida, H.; Shiina, Y.; Oishic, S.; Tobita, S. Reevaluation of absolute luminescence quantum yields of standard solutions using a spectrometer with an integrating sphere and a back-thinned CCD detector. Phys. Chem. Chem. Phys. 2009, 11, 985–9860. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds 1–7 are available from the authors. |
1·2DMSO | 2·4DMF·C4H8O2·H2O | 3·2DMF·4H2O | 4·2CH4O·3H2O | 5·2CH4O·2H2O | 6·4DMSO | 7·2H2O | |
---|---|---|---|---|---|---|---|
Formula | C56H90F12N6O22S10 Zn2 | C88.5H123.5N11.5O24S4Zn2 | C54H86N8O18Zn2 | C140H170N12O31Zn4 | C70H84N6O19Zn2 | C76H98N6O20S4Zn2 | C68H78N6O18Zn2 |
Formula Weight | 1878.82 | 1991.55 | 1266.09 | 2778.36 | 1444.21 | 1674.62 | 1398.10 |
Crystal system | Monoclinic | Triclinic | Monoclinic | Monoclinic | Triclinic | Triclinic | Triclinic |
Crystal size (mm) | 0.39 × 0.37 × 0.31 | 0.45 × 0.39 × 0.32 | 0.46 × 0.41 × 0.29 | 0.39 × 0.26 × 0.22 | 0.43 × 0.40 × 0.32 | 0.46 × 0.38 × 0.35 | 0.39 × 0.36 × 0.28 |
Space group | P21/c | P-1 | P21/c | P2(1)/c | P-1 | P-1 | P-1 |
a (Å) | 12.5300(12) | 14.7692(3) | 9.6799(4) | 18.596(4) | 11.0068(4) | 11.6847(5) | 10.2345(4) |
b (Å) | 20.941(2) | 18.9886(4) | 16.4617(8) | 9.6191(19) | 11.8259(4) | 11.7317(5) | 15.3764(8) |
c (Å) | 18.1657(16) | 19.1344(4) | 20.8877(9) | 39.263(8) | 16.1201(5) | 15.8174(6) | 22.3239(12) |
α (°) | 90 | 90.3180(10) | 90 | 90 | 74.221(3) | 90.703(2) | 86.275(4) |
β (°) | 123.313(5) | 107.6140(10) | 110.758(2) | 91.81(3) | 87.726(3) | 93.460(2) | 89.799(4) |
γ (°) | 90 | 104.8680(10) | 90 | 90 | 64.877(3) | 114.094(2) | 73.514(4) |
V (Å3) | 3983.3(6) | 4923.15(18) | 3112.3(2) | 7020(2) | 1821.26(11) | 1974.13(14) | 3361.2(3) |
Z | 2 | 2 | 2 | 2 | 1 | 1 | 2 |
Dcalc (Mg m−3) | 1.566 | 1.343 | 1.351 | 1.314 | 1.317 | 1.409 | 1.381 |
μ (mm−1) | 0.964 | 0.648 | 0.844 | 0.752 | 0.731 | 0.788 | 0.789 |
F (000) | 1944 | 2120 | 1340 | 2924 | 758 | 880 | 1464 |
No. Rfl. unique | 12158 | 29649 | 8393 | 17545 | 9039 | 8948 | 16660 |
No. Rfl. observed | 10353 | 21994 | 6634 | 9294 | 7033 | 5891 | 8622 |
R | 0.0502 | 0.0550 | 0.0365 | 0.0607 | 0.0615 | 0.0440 | 0.0709 |
wR | 0.1388 | 0.1615 | 0.1152 | 0.1403 | 0.1871 | 0.1063 | 0.1504 |
R for all | 0.0596 | 0.0794 | 0.0520 | 0.1282 | 0.0792 | 0.0952 | 0.1487 |
wR for all | 0.1457 | 0.1827 | 0.1258 | 0.1756 | 0.2047 | 0.1397 | 0.1934 |
GOF | 1.019 | 1.008 | 1.022 | 1.005 | 1.014 | 1.018 | 1.013 |
CCDC number | 968282 | 1526883 | 846596 | 968278 | 968279 | 968280 | 968281 |
Complex | 4 | 5 | 6 | 7 | |
---|---|---|---|---|---|
Step 1 | a, °C | 60–126 | 120–200 | 130–158 | 60–215 |
b, % | 5.1 | 9.2 | 8.8 | 13.5 | |
Step 2 | a, °C | 276–422 | 249–454 | 256–463 | 236–448 |
b, % | 44.2 | 45.6 | 30.2 | 38.3 | |
Step 3 | a, °C | 422–674 | 454–550 | 463–518 | 448–569 |
b, % | 38.2 | 31.5 | 14.4 | 36.0 | |
Step 4 | a, °C | 518–593 | |||
b, % | 24.2 |
Bands, nm | L1 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | ||
---|---|---|---|---|---|---|---|---|---|---|
Solid state | Exmax | 310 | 340 | 360 | 315 | 350 | 355 | 304 | 300 | |
Emmax | 413 | 463 | 462 | 383 | 390 | 425 | 388 | 411 | ||
Solvent | DMF a | Exmax | 306 | 342 | 310 | 308 | 309 | 344 | 354 | 327 |
Emmax | 356 | 411 | 412 | 390 | 399 | 416 | 446 | 425 | ||
DMSO a | Exmax | 300 | 350 | 360 | 300 | 300 | 325 | 315 | 330 | |
Emmax | 380 | 440 | 440 | 395 | 396 | 408 | 379 | 402 |
Solvent | Parameters | L1 | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|---|---|---|---|
DMF | Gradx | 30,664 | 212,755 | 221,420 | 233,883 | 40,170 | 766,539 | 38,980 | 3542 |
R2 | 0.9991 | 0.9989 | 0.9919 | 0.9994 | 0.9990 | 0.9989 | 0.9883 | 0.9952 | |
Φ | 0.0042 | 0.0293 | 0.0305 | 0.0322 | 0.0055 | 0.1057 | 0.0054 | 0.0005 | |
DMSO | Grad | 138,805 | 319,677 | 281,248 | 95,396 | 265,597 | 829,585 | 126,016 | 71,006 |
R2 | 0.9986 | 0.9900 | 0.9996 | 0.9916 | 0.9972 | 0.9977 | 0.9920 | 0.9939 | |
Φx | 0.0205 | 0.0473 | 0.0416 | 0.0141 | 0.0393 | 0.1227 | 0.0186 | 0.0105 |
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Xue, X.; Wang, Q.; Mai, F.; Liang, X.; Huang, Y.; Li, J.; Zhou, Y.; Yang, D.; Ma, Z. Study on the Photoluminescent and Thermal Properties of Zinc Complexes with a N6O4 Macrocyclic Ligand. Molecules 2018, 23, 1735. https://doi.org/10.3390/molecules23071735
Xue X, Wang Q, Mai F, Liang X, Huang Y, Li J, Zhou Y, Yang D, Ma Z. Study on the Photoluminescent and Thermal Properties of Zinc Complexes with a N6O4 Macrocyclic Ligand. Molecules. 2018; 23(7):1735. https://doi.org/10.3390/molecules23071735
Chicago/Turabian StyleXue, Xingyong, Qijun Wang, Fusen Mai, Xing Liang, Yichen Huang, Jiahe Li, Yanling Zhou, Dengfeng Yang, and Zhen Ma. 2018. "Study on the Photoluminescent and Thermal Properties of Zinc Complexes with a N6O4 Macrocyclic Ligand" Molecules 23, no. 7: 1735. https://doi.org/10.3390/molecules23071735