Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence

Arthur H.G. David; Amine Garci; Seifallah Abid; Xuesong Li; Ryan Michael Young; James S.W. Seale; Jessica Elizabeth Hornick; Chandra S. Azad; Yang Jiao; Indranil Roy; Isil Akpinar; Tanay Kesharwani; Charlotte L. Stern; Michael R. Wasielewski; J. Fraser Stoddart

doi:10.1021/jacs.3c01244

Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence

Arthur H.G. David, Amine Garci, Seifallah Abid, Xuesong Li, Ryan Michael Young^*, James S.W. Seale, Jessica Elizabeth Hornick, Chandra S. Azad, Yang Jiao, Indranil Roy, Isil Akpinar, Tanay Kesharwani, Charlotte L. Stern, Michael R. Wasielewski^*, J. Fraser Stoddart^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Near-infrared (NIR) light is known to have outstanding optical penetration in biological tissues and to be non-invasive to cells compared with visible light. These characteristics make NIR-specific light optimal for numerous biological applications, such as the sensing of biomolecules or in theranostics. Over the years, significant progress has been achieved in the synthesis of fluorescent cyclophanes for sensing, bioimaging, and making optoelectronic materials. The preparation of NIR-emissive porphyrin-free cyclophanes is, however, still challenging. In an attempt for fluorescence emissions to reach into the NIR spectral region, employing organic tetracationic cyclophanes, we have inserted two 9,10-divinylanthracene units between two of the pyridinium units in cyclobis(paraquat-p-phenylene). Steady-state absorption, fluorescence, and transient-absorption spectroscopies reveal the deep-red and NIR photoluminescence of this cyclophane. This tetracationic cyclophane is highly soluble in water and has been employed successfully as a probe for live-cell imaging in a breast cancer cell line (MCF-7).

Original language	English (US)
Pages (from-to)	9182-9190
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	145
Issue number	16
DOIs	https://doi.org/10.1021/jacs.3c01244
State	Published - Apr 26 2023

Funding

The authors would like to thank Northwestern University (NU) for their continued support of this research. The authors acknowledge the Integrated Molecular Structure Education and Research Center (IMSERC) at NU and the Northwestern University Biological Imaging Facility (RRID: SCR_017767) for providing access to equipment for the experiments. The Biological Imaging Facility at Northwestern University is generously supported by the Chemistry for Life Processes Institute, the Department of Molecular Biosciences, the Rice Foundation, and the NU Office for Research. This project was also supported by the National Science Foundation under grant number DMR-2003739 (M.R.W. and R.M.Y.). This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under contract no. DE-AC02-06CH11357. The use of the LS-CAT Sector 21 was supported by the Michigan Economic Development Corporation and the Michigan Technology Tri-Corridor (grant 085P1000817). J.S.W.S. gratefully acknowledges support from the Ryan Fellowship and the International Institute for Nanotechnology at Northwestern University. The authors thank Paige J. Brown for her assistance on the fluorescence measurement.

ASJC Scopus subject areas

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jacs.3c01244

Cite this

David, A. H. G., Garci, A., Abid, S., Li, X., Young, R. M., Seale, J. S. W., Hornick, J. E., Azad, C. S., Jiao, Y., Roy, I., Akpinar, I., Kesharwani, T., Stern, C. L., Wasielewski, M. R., & Stoddart, J. F. (2023). Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence. Journal of the American Chemical Society, 145(16), 9182-9190. https://doi.org/10.1021/jacs.3c01244

@article{fb229787afef41b69ed4affba278e280,

title = "Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence",

abstract = "Near-infrared (NIR) light is known to have outstanding optical penetration in biological tissues and to be non-invasive to cells compared with visible light. These characteristics make NIR-specific light optimal for numerous biological applications, such as the sensing of biomolecules or in theranostics. Over the years, significant progress has been achieved in the synthesis of fluorescent cyclophanes for sensing, bioimaging, and making optoelectronic materials. The preparation of NIR-emissive porphyrin-free cyclophanes is, however, still challenging. In an attempt for fluorescence emissions to reach into the NIR spectral region, employing organic tetracationic cyclophanes, we have inserted two 9,10-divinylanthracene units between two of the pyridinium units in cyclobis(paraquat-p-phenylene). Steady-state absorption, fluorescence, and transient-absorption spectroscopies reveal the deep-red and NIR photoluminescence of this cyclophane. This tetracationic cyclophane is highly soluble in water and has been employed successfully as a probe for live-cell imaging in a breast cancer cell line (MCF-7).",

author = "David, {Arthur H.G.} and Amine Garci and Seifallah Abid and Xuesong Li and Young, {Ryan Michael} and Seale, {James S.W.} and Hornick, {Jessica Elizabeth} and Azad, {Chandra S.} and Yang Jiao and Indranil Roy and Isil Akpinar and Tanay Kesharwani and Stern, {Charlotte L.} and Wasielewski, {Michael R.} and Stoddart, {J. Fraser}",

note = "Funding Information: The authors would like to thank Northwestern University (NU) for their continued support of this research. The authors acknowledge the Integrated Molecular Structure Education and Research Center (IMSERC) at NU and the Northwestern University Biological Imaging Facility (RRID: SCR_017767) for providing access to equipment for the experiments. The Biological Imaging Facility at Northwestern University is generously supported by the Chemistry for Life Processes Institute, the Department of Molecular Biosciences, the Rice Foundation, and the NU Office for Research. This project was also supported by the National Science Foundation under grant number DMR-2003739 (M.R.W. and R.M.Y.). This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under contract no. DE-AC02-06CH11357. The use of the LS-CAT Sector 21 was supported by the Michigan Economic Development Corporation and the Michigan Technology Tri-Corridor (grant 085P1000817). J.S.W.S. gratefully acknowledges support from the Ryan Fellowship and the International Institute for Nanotechnology at Northwestern University. The authors thank Paige J. Brown for her assistance on the fluorescence measurement. Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = apr,

day = "26",

doi = "10.1021/jacs.3c01244",

language = "English (US)",

volume = "145",

pages = "9182--9190",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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David, AHG, Garci, A, Abid, S, Li, X, Young, RM, Seale, JSW, Hornick, JE, Azad, CS, Jiao, Y, Roy, I, Akpinar, I, Kesharwani, T, Stern, CL, Wasielewski, MR & Stoddart, JF 2023, 'Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence', Journal of the American Chemical Society, vol. 145, no. 16, pp. 9182-9190. https://doi.org/10.1021/jacs.3c01244

TY - JOUR

T1 - Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence

AU - David, Arthur H.G.

AU - Garci, Amine

AU - Abid, Seifallah

AU - Li, Xuesong

AU - Young, Ryan Michael

AU - Seale, James S.W.

AU - Hornick, Jessica Elizabeth

AU - Azad, Chandra S.

AU - Jiao, Yang

AU - Roy, Indranil

AU - Akpinar, Isil

AU - Kesharwani, Tanay

AU - Stern, Charlotte L.

AU - Wasielewski, Michael R.

AU - Stoddart, J. Fraser

N1 - Funding Information: The authors would like to thank Northwestern University (NU) for their continued support of this research. The authors acknowledge the Integrated Molecular Structure Education and Research Center (IMSERC) at NU and the Northwestern University Biological Imaging Facility (RRID: SCR_017767) for providing access to equipment for the experiments. The Biological Imaging Facility at Northwestern University is generously supported by the Chemistry for Life Processes Institute, the Department of Molecular Biosciences, the Rice Foundation, and the NU Office for Research. This project was also supported by the National Science Foundation under grant number DMR-2003739 (M.R.W. and R.M.Y.). This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under contract no. DE-AC02-06CH11357. The use of the LS-CAT Sector 21 was supported by the Michigan Economic Development Corporation and the Michigan Technology Tri-Corridor (grant 085P1000817). J.S.W.S. gratefully acknowledges support from the Ryan Fellowship and the International Institute for Nanotechnology at Northwestern University. The authors thank Paige J. Brown for her assistance on the fluorescence measurement. Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/4/26

Y1 - 2023/4/26

N2 - Near-infrared (NIR) light is known to have outstanding optical penetration in biological tissues and to be non-invasive to cells compared with visible light. These characteristics make NIR-specific light optimal for numerous biological applications, such as the sensing of biomolecules or in theranostics. Over the years, significant progress has been achieved in the synthesis of fluorescent cyclophanes for sensing, bioimaging, and making optoelectronic materials. The preparation of NIR-emissive porphyrin-free cyclophanes is, however, still challenging. In an attempt for fluorescence emissions to reach into the NIR spectral region, employing organic tetracationic cyclophanes, we have inserted two 9,10-divinylanthracene units between two of the pyridinium units in cyclobis(paraquat-p-phenylene). Steady-state absorption, fluorescence, and transient-absorption spectroscopies reveal the deep-red and NIR photoluminescence of this cyclophane. This tetracationic cyclophane is highly soluble in water and has been employed successfully as a probe for live-cell imaging in a breast cancer cell line (MCF-7).

AB - Near-infrared (NIR) light is known to have outstanding optical penetration in biological tissues and to be non-invasive to cells compared with visible light. These characteristics make NIR-specific light optimal for numerous biological applications, such as the sensing of biomolecules or in theranostics. Over the years, significant progress has been achieved in the synthesis of fluorescent cyclophanes for sensing, bioimaging, and making optoelectronic materials. The preparation of NIR-emissive porphyrin-free cyclophanes is, however, still challenging. In an attempt for fluorescence emissions to reach into the NIR spectral region, employing organic tetracationic cyclophanes, we have inserted two 9,10-divinylanthracene units between two of the pyridinium units in cyclobis(paraquat-p-phenylene). Steady-state absorption, fluorescence, and transient-absorption spectroscopies reveal the deep-red and NIR photoluminescence of this cyclophane. This tetracationic cyclophane is highly soluble in water and has been employed successfully as a probe for live-cell imaging in a breast cancer cell line (MCF-7).

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U2 - 10.1021/jacs.3c01244

DO - 10.1021/jacs.3c01244

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C2 - 37042705

AN - SCOPUS:85152691088

SN - 0002-7863

VL - 145

SP - 9182

EP - 9190

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 16

ER -

Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence

Abstract

Funding

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CCDC 2161003: Experimental Crystal Structure Determination

CCDC 2161001: Experimental Crystal Structure Determination

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Divinylanthracene-Containing Tetracationic Organic Cyclophane with Near-Infrared Photoluminescence

Abstract

Funding

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2161003: Experimental Crystal Structure Determination

CCDC 2161001: Experimental Crystal Structure Determination

Cite this