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  • 1.
    Bornhof, Anna-Bea
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Xiong, Ruisheng
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Rational Synthesis of 2-Bromoporphyrins and 2,12-Dibromoporphyrins2017In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 23, p. 12908-12913Article in journal (Refereed)
    Abstract [en]

    Bromoporphyrins were prepared by the metal-mediated self-condensation of brominated 1-formyldipyrromethanes. Depending on the conditions, Mg(II)-2,12-dibromoporphyrin and Mg(II)-2-bromoporphyrin could be obtained in up to 11% and 17% isolated yield, respectively. Zn(II) was also a viable templating metal. The positions of the bromine substituents were confirmed by 2D-NMR spectroscopic analysis and the X-ray crystal structure of a derivative. Suzuki and Sonogashira reactions of the bromoporphyrins yielded 2-substituted or 2,12-disubstituted porphyrins with red-shifted absorption and emission spectra. This method provides access to the minimalist core of beta-mono- and beta,beta'-disubstituted porphyrins from readily available starting materials.

  • 2.
    Xiong, Ruisheng
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Development of Novel Hydroporphyrins for Light Harvesting and Sensitising NIR Lanthanide Luminescence2017Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Chlorins, as the core structures of chlorophylls, have been extensively studied for harvesting solar energy, fluorescent imaging and photodynamic therapy against cancer. This thesis is concerned with design and synthesis of novel chlorins as antennae for harvesting light and sensitising near infrared lanthanide luminescence.

    In the first part, a series of chlorin monomers, dimers and polymers were synthesised and their photophysical properties were characterised. The chlorin monomers were substituted with five-membered heterocycles, such as thiophenes and furans. These heterocycles function as auxochromes analogous to the natural ones in chlorophylls, and extend chlorin absorption and emission strongly to the red (up to λem = 680 nm). A borylation method was developed to prepare borylated chlorins, which gave access to directly linked chlorin dimers through Suzuki coupling reaction. Different regioisomers of chlorin dimer were prepared, including β-meso homodimers, meso-meso homodimers and heterodimers. The dimerisation resulted in red-shifted absorption and emission. Chlorin polymerisations were performed both electrochemically and chemically. Bis-thienylchlorins yielded chlorin films and an organic solvent soluble copolymer with hexylthiophene, respectively. These polymers from both polymerisations have red absorptions beyond 700 nm, and might be used as light-harvesting antennae.

    In the second part, chlorins were used as chromophores to sensitise near infrared lanthanide luminescence. Two types of chlorin-lanthanide dyads were prepared through lanthanide coordination with cyclen derivatives and dipicolinic acids (DPA). The cyclen-based dyads were poorly soluble in water, thus their near infrared emissions were not observed. The other type of complexes was fully soluble in H2O and THF. Both Nd and Yb emission were recorded even upon excitation into the Q bands of chlorins. In the dyads with free base chlorins, the singlet state of chlorins might be involved in the sensitisation of lanthanide luminescence. These DPA-based dyads presented two-color emission based on one chlorin and two-color excitation based on one lanthanide ion. These dyads would enable in theory 4-color imaging.

    In the last part, a microwave-assisted two-step synthesis was described to prepare dipyrromethanes, which are the key intermediates in the chlorin synthesis. This mild method took advantage of the nucleophilicity of pyrrole and the electrophilicity of N,N-dimethylaminomethyl pyrroles. The usually used acid catalysis is detrimental to many functionalities, thus our methods enable the synthesis of dipyrromethanes with acid sensitive groups or a formyl group.

    List of papers
    1. Furan- and Thiophene-Based Auxochromes Red-shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations
    Open this publication in new window or tab >>Furan- and Thiophene-Based Auxochromes Red-shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations
    Show others...
    2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 17, p. 4089-4095Article in journal (Refereed) Published
    Abstract [en]

    The de novo syntheses of chemically stable chlorins with five-membered heterocyclic (furane, thiophene, formylfurane and formylthiophene) substituents in selected meso- and beta-positions are reported. Heterocycle incorporation in the 3- and 13-positions shifted the chlorin absorption and emission to the red (up to lambdaem =680 nm), thus these readily incorporated substituents function analogously to auxochromes present in chlorophylls, for example, formyl and vinyl groups. Photophysical, theoretical and X-ray crystallographic experiments revealed small but significant differences between the behavior of the furan- and the thiophene-based auxochromes. Four regioisomeric bis-thienylchlorins (3,10; 3,13, 3,15 and 10,15) were oxidatively electropolymerized; the chlorin monomer geometry had a profound impact on the polymerization efficiency and the electrochemical properties of the resulting material. Chemical co-polymerization of 3,13-bis-thienylchlorin with 3-hexylthiophene yielded an organic-soluble red-emitting polymer.

    Keywords
    chlorins, electrochemistry, photophysics, polymerization, porphyrinoids
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-317978 (URN)10.1002/chem.201604655 (DOI)000399312700011 ()27859811 (PubMedID)
    Funder
    Stiftelsen Olle Engkvist ByggmästareSwedish Research Council, 2013-4655Swedish Research Council, 2013-4763
    Available from: 2017-03-22 Created: 2017-03-22 Last updated: 2017-12-28Bibliographically approved
    2. Directly linked hydroporphyrin dimers
    Open this publication in new window or tab >>Directly linked hydroporphyrin dimers
    Show others...
    2016 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, no 58, p. 9056-9058Article in journal (Refereed) Published
    Abstract [en]

    Directly linked hydroporphyrin (chlorin) dimers were accessed regioselectively from bromochlorins. Versatile 15-borylated chlorins were prepared in excellent yield via Miyaura borylation. Suzuki coupling yielded meso-beta-linked homo- and heterodimers, and meso-blinked dimers. The photophysical and electrochemical properties of the dimers are reported.

    National Category
    Other Chemistry Topics
    Identifiers
    urn:nbn:se:uu:diva-300581 (URN)10.1039/c6cc00516k (DOI)000379431000018 ()26859412 (PubMedID)
    Funder
    Swedish Research Council, 2013-4655Stiftelsen Olle Engkvist Byggmästare
    Available from: 2016-08-09 Created: 2016-08-09 Last updated: 2017-11-28Bibliographically approved
    3. Synthesis and characterisation of lanthanide-hydroporphyrin dyads
    Open this publication in new window or tab >>Synthesis and characterisation of lanthanide-hydroporphyrin dyads
    2015 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 44, p. 2541-2553Article in journal (Refereed) Published
    Abstract [en]

    Fluorescence spectroscopy is in many ways the ideal tool for the interrogation of complex biological systems, as it is non-invasive, sensitive, and offers high spatiotemporal resolution. For biomedical imaging luminescent probes absorbing and emitting in the red-to-near infrared (NIR) region are best suited to maximise tissue penetration and minimise damage to cellular components. NIR-emitting lanthanides (Ln) sensitised with red-absorbing antennae are promising candidates for these applications, assuming the challenges of poor photophysical properties and tedious syntheses of the complexes are overcome. Chlorins are porphyrin-type tetrapyrroles with intense red absorption. Recently chlorins have been shown to sensitise Yb and Nd emission when incorporated into Ln-complexes. Here we expand on our previous work, and explore the effect of chlorin structure, metallation state, chlorin-Ln-complex linker length and mode of attachment on the properties of chlorin-Ln complexes. As chlorin absorption bands are approximately 20 nm fwhm and readily tunable, a deeper understanding of structure-property relationships would enable the use of chlorin-Ln complexes in multicolour imaging using antenna-specific excitation. A detailed description of antenna and complex syntheses and photophysical characterisation is given. A number of challenges were identified, which will have to be addressed in future studies to enable multicolour imaging using the NIR-emitting lanthanides.

    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-317982 (URN)
    Funder
    Swedish Research Council, 2013-4655Stiftelsen Olle Engkvist Byggmästare
    Available from: 2017-03-22 Created: 2017-03-22 Last updated: 2017-11-29
    4. Excitation- and emission wavelength-based multiplex imaging using red-absorbing near infrared-emitting lanthanide complexes
    Open this publication in new window or tab >>Excitation- and emission wavelength-based multiplex imaging using red-absorbing near infrared-emitting lanthanide complexes
    (English)Manuscript (preprint) (Other academic)
    Abstract [en]

    : Multiplex luminescence imaging in the red and near infrared (NIR) should be an enabling tool for the real-time investigation of complex biological systems. Current probes have numerous limitations including low photostability, short luminescent lifetime, overlapping absorption and emission bands, and small Stokes shift, the combination of which limits multiplexing in this region to two colors. Here we report emitters based on near infrared (NIR) emitting luminescent lanthanides (Ln) sensitized by hydroporphyin antennae. The narrow and intense absorption bands of hydroporphyrins are in the red, and their porisiotns are readily tunable. These dyads enable both emission- and excitation-based multiplexing; the former by combining either the same antenna with different Ln’s, the latter by attaching chlorin antennae with non-overlapping absorptions to the same Ln-complex. Up to 4 different species could be discerned without tedious data manipulation.

    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-319907 (URN)
    Available from: 2017-04-10 Created: 2017-04-10 Last updated: 2017-04-10
    5. Mild Microwave-Assisted Synthesis of Dipyrromethanes and Their Analogues
    Open this publication in new window or tab >>Mild Microwave-Assisted Synthesis of Dipyrromethanes and Their Analogues
    2014 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 26, p. 484-488Article in journal (Refereed) Published
    Abstract [en]

    The Mannich reaction between pyrroles or indoles and Eschenmoser’s salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2- and 3-sub- stituted derivatives could be obtained. The N,N-dimethylaminometh- ylpyrroles and indoles underwent substitution with pyrrole under mi- crowave irradiation, affording the appropriate dipyrromethanes, N- confused, and indolo-dipyrromethanes in moderate to excellent overall yield. 

    Keywords
    pyrroles, indoles, heterocycles, microwave synthesis, dipyrromethanes
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-317983 (URN)10.1055/s-0034-1378925 (DOI)
    Funder
    Swedish Research Council, 2013-4655
    Available from: 2017-03-22 Created: 2017-03-22 Last updated: 2017-11-29
  • 3.
    Xiong, Ruisheng
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Paramagnetic ligand tagging to identify ligand-protein binding sites2018Conference paper (Refereed)
    Abstract [en]

    Ligand-protein interactions are pivotal in living organisms. Knowing the binding sites of small-molecule ligands, especially low affinity ones, is an important step for modern drug discovery as it enables the development of high affinity lead compounds. Due to the lack of robust characterization approaches, the determination of weak binding is still cumbersome. We have reported a paramagnetic ligand tagging method by taking advantage of pseudo-contact shifts of protein NMR, which requires the ligand to be linked to a paramagnetic lanthanide complex.1 In this project we have improved the structure of our original paramagnetic tag to increase the accuracy of the NMR-based  structure determination as compared to our previously presented approach.

  • 4.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Andres, Julien
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Scheffler, Kira
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Borbas, Eszter K.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Synthesis and characterisation of lanthanide-hydroporphyrin dyads2015In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 44, no 6, p. 2541-2553Article in journal (Refereed)
    Abstract [en]

    Fluorescence spectroscopy is in many ways the ideal tool for the interrogation of complex biological systems, as it is non-invasive, sensitive, and offers high spatiotemporal resolution. For biomedical imaging luminescent probes absorbing and emitting in the red-to-near infrared (NIR) region are best suited to maximise tissue penetration and minimise damage to cellular components. NIR-emitting lanthanides (Ln) sensitised with red-absorbing antennae are promising candidates for these applications, assuming the challenges of poor photophysical properties and tedious syntheses of the complexes are overcome. Chlorins are porphyrin-type tetrapyrroles with intense red absorption. Recently chlorins have been shown to sensitise Yb and Nd emission when incorporated into Ln-complexes. Here we expand on our previous work, and explore the effect of chlorin structure, metallation state, chlorin-Ln-complex linker length and mode of attachment on the properties of chlorin-Ln complexes. As chlorin absorption bands are similar to 20 nm fwhm and readily tunable, a deeper understanding of structure-property relationships would enable the use of chlorin-Ln complexes in multicolour imaging using antenna-specific excitation. A detailed description of antenna and complex syntheses and photophysical characterisation is given. A number of challenges were identified, which will have to be addressed in future studies to enable multicolour imaging using the NIR-emitting lanthanides.

  • 5.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Arkhypchuk, Anna I.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Attempted syntheses of N-confused hydroporphyrins through modified Lindsey routes2019In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, no 4-5, p. 589-598Article in journal (Refereed)
    Abstract [en]

    Unlike N-confused porphyrins which are well-known and extensively studied tetrapyrroles, N-confused hydroporphyrins are almost unknown, largely because so far they have resisted attempts at rational synthesis. Here, we report our efforts towards the total synthesis of N-confused hydroporphyrins. We have prepared N-confused building blocks analogous to the non-N-confused substrates in the Lindsey synthesis of sparsely substituted chlorins. We have systematically flipped the A, B and C pyrrole rings in the dipyrrolic precursors of the target N-confused macrocycles, preparing in total an N-confused "Western half' (tetrahydrodipyrrin) and two N-confused "Eastern halves" (brominated formyldipyrromethanes). These were subjected to a range of cyclization conditions. While we successfully isolated and identified three macrocyclic products, none of these proved to be the desired N-confused hydroporphyrin.

  • 6.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Arkhypchuk, Anna I.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Kovacs, Daniel
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Directly linked hydroporphyrin dimers2016In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, no 58, p. 9056-9058Article in journal (Refereed)
    Abstract [en]

    Directly linked hydroporphyrin (chlorin) dimers were accessed regioselectively from bromochlorins. Versatile 15-borylated chlorins were prepared in excellent yield via Miyaura borylation. Suzuki coupling yielded meso-beta-linked homo- and heterodimers, and meso-blinked dimers. The photophysical and electrochemical properties of the dimers are reported.

  • 7.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Borbas, Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Design, synthesis, and characterization of a hydroporphyrin scaffold for the rational preparation of heterobimetallic lanthanide complexes2014In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 248Article in journal (Other academic)
  • 8.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Excitation- and emission-based multiplexing with near infrared-emitting luminescent lanthanide complexes using red-light excitation2017In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 253Article in journal (Other academic)
  • 9.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Mild Microwave-Assisted Synthesis of Dipyrromethanes and Their Analogues2015In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 26, no 4, p. 484-488Article in journal (Refereed)
    Abstract [en]

    The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2- and 3-substituted derivatives could be obtained. The N,N-dimethylaminomethylpyrroles and indoles underwent substitution with pyrrole under microwave irradiation, affording the appropriate dipyrromethanes, N-confused, and indolo-dipyrromethanes in moderate to excellent overall yield.

  • 10.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Bornhof, Anna-Bea
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Arkhypchuk, Anna
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Borbas, Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Furan- and Thiophene-Based Auxochromes Red-shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations2017In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 17, p. 4089-4095Article in journal (Refereed)
    Abstract [en]

    The de novo syntheses of chemically stable chlorins with five-membered heterocyclic (furane, thiophene, formylfurane and formylthiophene) substituents in selected meso- and beta-positions are reported. Heterocycle incorporation in the 3- and 13-positions shifted the chlorin absorption and emission to the red (up to lambdaem =680 nm), thus these readily incorporated substituents function analogously to auxochromes present in chlorophylls, for example, formyl and vinyl groups. Photophysical, theoretical and X-ray crystallographic experiments revealed small but significant differences between the behavior of the furan- and the thiophene-based auxochromes. Four regioisomeric bis-thienylchlorins (3,10; 3,13, 3,15 and 10,15) were oxidatively electropolymerized; the chlorin monomer geometry had a profound impact on the polymerization efficiency and the electrochemical properties of the resulting material. Chemical co-polymerization of 3,13-bis-thienylchlorin with 3-hexylthiophene yielded an organic-soluble red-emitting polymer.

  • 11.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Erdelyi, Mate
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Paramagnetic lanthanide tags for identifying ligand-protein binding site2018Conference paper (Refereed)
    Abstract [en]

    Ligand-protein interactions are pivotal in living organisms. Knowing the binding sites of small-molecule ligands, especially low affinity ones, is an important step for modern drug discovery as it enables the development of high affinity lead compounds. Due to the lack of robust characterization approaches, the determination of weak binding is still cumbersome. We have reported a paramagnetic ligand tagging method by taking advantage of pseudo-contact shifts of protein NMR, which requires the ligand to be linked to a paramagnetic lanthanide complex.1 In this project we have improved the structure of our original paramagnetic tag to increase the accuracy of the NMR-based  structure determination as compared to our previously presented approach. 

  • 12.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Mara, Dimitrije
    Univ Ghent, Dept Chem, L3, Krijgslaan 281,Bldg S3, B-9000 Ghent, Belgium.
    Liu, Jing
    Univ Ghent, Dept Chem, L3, Krijgslaan 281,Bldg S3, B-9000 Ghent, Belgium.
    Van Deun, Rik
    Univ Ghent, Dept Chem, L3, Krijgslaan 281,Bldg S3, B-9000 Ghent, Belgium.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Excitation- and Emission-Wavelength-Based Multiplex Spectroscopy Using Red-Absorbing Near-Infrared-Emitting Lanthanide Complexes2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 35, p. 10975-10979Article in journal (Refereed)
    Abstract [en]

    Multiplex imaging in the red and near-infrared (NIR) should be an enabling tool for the real-time investigation of biological systems. Currently available emitters have short luminescent lifetimes, broad absorption and emission bands, and small Stokes shifts, which limits multiplexing in this region to two colors. NIR-emitting luminescent lanthanide (Ln) complexes carrying hydroporphyrin (chlorin) sensitizing antennae are excitable in the red through the narrow, intense and tunable chlorin absorptions. Both emission- and excitation-based multiplexing are possible, the former by exciting the same antenna appended to different Lns, the latter by attaching different chlorins with nonoverlapping absorptions to the same Ln. The combination of excitation and emission spectroscopies allows for the straightforward differentiation of up to four different complexes.

1 - 12 of 12
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