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
M3 - Article
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 -
