ACS Publications. Most Trusted. Most Cited. Most Read
Synthesis of Chlorin-Sensitized Near Infrared-Emitting Lanthanide Complexes

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Inorg. Chem. 2012, 51, 19, 10366-10374
    Article

    Synthesis of Chlorin-Sensitized Near Infrared-Emitting Lanthanide Complexes
    Click to copy article linkArticle link copied!

    View Author Information
    † Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691, Stockholm, Sweden
    ‡ Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, U.K.
    § Department of Chemistry−BMC, Uppsala University, SE-75123, Uppsala, Sweden
    *E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    Inorganic Chemistry

    Cite this: Inorg. Chem. 2012, 51, 19, 10366–10374
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ic3015354
    Published September 14, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Lanthanide (Yb3+, Nd3+) complexes equipped with red-absorbing hydroporphyrin (chlorin) antennae were synthesized and characterized. The syntheses are scalable, highly modular, and enable the introduction of different chlorins functionalized with a single reactive group (COOH or NH2). Absorption maxima were dependent on chlorin substitution pattern (monomeso aryl or dimeso aryl) and metalation state (free base or zinc chelate). The complexes benefit from dual chlorin (610–639 nm) and lanthanide (980 or 1065 nm for Yb- or Nd-complexes, respectively) emission in the biologically relevant red and near IR region of the spectrum.

    Copyright © 2012 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Additional synthetic procedures and spectral characterization, and copies of 1H and 13C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 28 publications.

    1. Mariia Faustova, Elena Nikolskaya, Maria Sokol, Margarita Fomicheva, Rem Petrov, Nikita Yabbarov. Metalloporphyrins in Medicine: From History to Recent Trends. ACS Applied Bio Materials 2020, 3 (12) , 8146-8171. https://doi.org/10.1021/acsabm.0c00941
    2. Ruisheng Xiong, Dimitrije Mara, Jing Liu, Rik Van Deun, K. Eszter Borbas. Excitation- and Emission-Wavelength-Based Multiplex Spectroscopy Using Red-Absorbing Near-Infrared-Emitting Lanthanide Complexes. Journal of the American Chemical Society 2018, 140 (35) , 10975-10979. https://doi.org/10.1021/jacs.8b07609
    3. Xun Feng, Yuquan Feng, Nan Guo, Yiling Sun, Tian Zhang, Lufang Ma, and Liya Wang . Series d–f Heteronuclear Metal–Organic Frameworks: Color Tunability and Luminescent Probe with Switchable Properties. Inorganic Chemistry 2017, 56 (3) , 1713-1721. https://doi.org/10.1021/acs.inorgchem.6b02851
    4. Jonathan S. Lindsey . De Novo Synthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World. Chemical Reviews 2015, 115 (13) , 6534-6620. https://doi.org/10.1021/acs.chemrev.5b00065
    5. Adam Meares, Andrius Satraitis, Nithya Santhanam, Zhanqian Yu, and Marcin Ptaszek . Deep-Red Emissive BODIPY–Chlorin Arrays Excitable with Green and Red Wavelengths. The Journal of Organic Chemistry 2015, 80 (8) , 3858-3869. https://doi.org/10.1021/acs.joc.5b00119
    6. Zhanqian Yu and Marcin Ptaszek . Near-IR Emissive Chlorin–Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength. The Journal of Organic Chemistry 2013, 78 (21) , 10678-10691. https://doi.org/10.1021/jo4016858
    7. Ingvild U. Hageberg, Katrianne Arja, Benedikte E. Vindstad, Johannes K. Bergvoll, Odrun A. Gederaas, Thor‐Bernt Melø, K. Peter R. Nilsson, Mikael Lindgren. Photophysics of Glycosylated Ring‐Fused Chlorin Complexes and Their Photosensitizing Effects on Cancer Cells. ChemPhotoChem 2023, 7 (8) https://doi.org/10.1002/cptc.202300028
    8. Masahiko Taniguchi, David F. Bocian, Dewey Holten, Jonathan S. Lindsey. Beyond green with synthetic chlorophylls – Connecting structural features with spectral properties. Journal of Photochemistry and Photobiology C: Photochemistry Reviews 2022, 52 , 100513. https://doi.org/10.1016/j.jphotochemrev.2022.100513
    9. Guo-Qing Jin, Calvin V. Chau, Jonathan F. Arambula, Song Gao, Jonathan L. Sessler, Jun-Long Zhang. Lanthanide porphyrinoids as molecular theranostics. Chemical Society Reviews 2022, 51 (14) , 6177-6209. https://doi.org/10.1039/D2CS00275B
    10. Petr Hermann, Jan Kotek, Vojtěch Kubíček. Ten-Membered Rings or Lager With One or More Nitrogen Atoms. 2022, 591-683. https://doi.org/10.1016/B978-0-12-818655-8.00128-1
    11. Daniel Kocsi, Daniel Kovacs, Jordann A. L. Wells, K. Eszter Borbas. Reduced quenching effect of pyridine ligands in highly luminescent Ln( iii ) complexes: the role of tertiary amide linkers. Dalton Transactions 2021, 50 (45) , 16670-16677. https://doi.org/10.1039/D1DT02893F
    12. Anais Biscotti, François Estour, Berthe-Sandra Sembo-Backonly, Sébastien Balieu, Michaël Bosco, Cécile Barbot, Agnès Pallier, Éva Tóth, Célia S. Bonnet, Géraldine Gouhier. Gd3+ Complexes Conjugated to Cyclodextrins: Hydroxyl Functions Influence the Relaxation Properties. Processes 2021, 9 (2) , 269. https://doi.org/10.3390/pr9020269
    13. K. Eszter Borbas. Analyte-Responsive Luminescent Dyes Based on Trivalent Lanthanide Coordination Compounds. 2021, 35-65. https://doi.org/10.1007/4243_2020_17
    14. Dinesh Balasooriya, Beibei Liu, Hongshan He, Andew Sykes, P. Stanley May. A conjugated porphyrin as a red-light sensitizer for near-infrared emission of ytterbium( iii ) ion. New Journal of Chemistry 2020, 44 (43) , 18756-18762. https://doi.org/10.1039/D0NJ04910G
    15. Anna I. Arkhypchuk, Ruisheng Xiong, K. Eszter Borbas. Investigation of the demetallation of 10-aryl substituted synthetic chlorins under acidic conditions. Journal of Inorganic Biochemistry 2020, 205 , 110979. https://doi.org/10.1016/j.jinorgbio.2019.110979
    16. Yingying Ning, Mengliang Zhu, Jun-Long Zhang. Near-infrared (NIR) lanthanide molecular probes for bioimaging and biosensing. Coordination Chemistry Reviews 2019, 399 , 213028. https://doi.org/10.1016/j.ccr.2019.213028
    17. Gabriel Brunet, Riccardo Marin, Melissa-Jane Monk, Ute Resch-Genger, Diogo A. Gálico, Fernando A. Sigoli, Elizaveta A. Suturina, Eva Hemmer, Muralee Murugesu. Exploring the dual functionality of an ytterbium complex for luminescence thermometry and slow magnetic relaxation. Chemical Science 2019, 10 (28) , 6799-6808. https://doi.org/10.1039/C9SC00343F
    18. Marcin Ptaszek. Hydroporphyrins in Fluorescence In Vivo Imaging. 2018, 21-51. https://doi.org/10.1007/978-3-030-01569-5_2
    19. Riikka Arppe, Nicolaj Kofod, Anne Kathrine R. Junker, Lea G. Nielsen, Elena Dallerba, Thomas Just Sørensen. Modulation of the Photophysical Properties of 1‐Azathioxanthones by Eu 3+ , Gd 3+ , Tb 3+ , and Yb 3+ Ions in Methanol. European Journal of Inorganic Chemistry 2017, 2017 (44) , 5246-5253. https://doi.org/10.1002/ejic.201700720
    20. Ruisheng Xiong, Anna‐Bea Bornhof, Anna I. Arkhypchuk, Andreas Orthaber, K. Eszter Borbas. Furan‐ and Thiophene‐Based Auxochromes Red‐shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations. Chemistry – A European Journal 2017, 23 (17) , 4089-4095. https://doi.org/10.1002/chem.201604655
    21. Paul Demay‐Drouhard, H. Y. Vincent Ching, Dmitry Akhmetzyanov, Régis Guillot, Leandro C. Tabares, Hélène C. Bertrand, Clotilde Policar. A Bis‐Manganese(II)–DOTA Complex for Pulsed Dipolar Spectroscopy. ChemPhysChem 2016, 17 (13) , 2066-2078. https://doi.org/10.1002/cphc.201600234
    22. Francesca Bryden, Ross W. Boyle. Metalloporphyrins for Medical Imaging Applications. 2016, 141-221. https://doi.org/10.1016/bs.adioch.2015.09.003
    23. Doyoung Ra, Kelly A. Gauger, Kannan Muthukumaran, Thiagarajan Balasubramanian, Vanampally Chandrashaker, Masahiko Taniguchi, Zhanqian Yu, Daniel C. Talley, Melanie Ehudin, Marcin Ptaszek, Jonathan S. Lindsey. Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability. Journal of Porphyrins and Phthalocyanines 2015, 19 (04) , 547-572. https://doi.org/10.1142/S1088424615500042
    24. Jonathan M. Yuen, Michelle A. Harris, Mengran Liu, James R. Diers, Christine Kirmaier, David F. Bocian, Jonathan S. Lindsey, Dewey Holten. Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 4: How Formyl Group Location Dictates the Spectral Properties of Chlorophylls b , d and f. Photochemistry and Photobiology 2015, 91 (2) , 331-342. https://doi.org/10.1111/php.12401
    25. Ruisheng Xiong, Julien Andres, Kira Scheffler, K. Eszter Borbas. Synthesis and characterisation of lanthanide-hydroporphyrin dyads. Dalton Transactions 2015, 44 (6) , 2541-2553. https://doi.org/10.1039/C4DT02448F
    26. Elias Pershagen, K. Eszter Borbas. Designing reactivity-based responsive lanthanide probes for multicolor detection in biological systems. Coordination Chemistry Reviews 2014, 273-274 , 30-46. https://doi.org/10.1016/j.ccr.2013.10.012
    27. Csongor Szíjjártó, Elias Pershagen, Nadia O. Ilchenko, K. Eszter Borbas. A Versatile Long‐Wavelength‐Absorbing Scaffold for Eu‐Based Responsive Probes. Chemistry – A European Journal 2013, 19 (9) , 3099-3109. https://doi.org/10.1002/chem.201203957
    28. Benjamin P. Burke, Stephen J. Archibald. Macrocyclic coordination chemistry. Annual Reports Section "A" (Inorganic Chemistry) 2013, 109 , 232. https://doi.org/10.1039/c3ic90032k
    Download PDF
    Go to Inorganic Chemistry
    Get e-Alerts
    Get e-Alerts

    Inorganic Chemistry

    Cite this: Inorg. Chem. 2012, 51, 19, 10366–10374
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ic3015354
    Published September 14, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

    Article Views

    2309

    Altmetric

    -

    Citations

    28
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.