logo

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2012, 77, 7, 3492-3500
RETURN TO ISSUEPREVArticleNEXT

Exhaustive Syntheses of Naphthofluoresceins and Their Functions

View Author Information
† Graduate School of Life and Environmental Sciences, Kyoto Prefectural University Shimogamo, Sakyo-ku Kyoto 606-8522, Japan
‡ Institute for Chemical Research, Kyoto University Uji, Kyoto, 611-0011, Japan
*[email protected]
Cite this: J. Org. Chem. 2012, 77, 7, 3492–3500
Publication Date (Web):March 19, 2012
https://doi.org/10.1021/jo300177b
Copyright © 2012 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
3003
Altmetric
-
Citations
40
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.

Read OnlinePDF (3 MB)
Get e-Alerts
Supporting Info (2)»
SUBJECTS:

Abstract

Abstract Image

Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel–Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.

Supporting Information

ARTICLE SECTIONS
Jump To

Coloration of seminaphthofluoresceines 8–10 under various pH conditions, calculated UV–vis spectrum, HOMO and LUMO of the dianion and cation of compound 5, 1H and 13C NMR spectra for all new compounds, and CIF of compound 5 (CCDC 862009). 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

This article is cited by 42 publications.

  1. Monica A. Gonzalez, Alison S. Walker, Kevin J. Cao, Julia R. Lazzari-Dean, Nicholas S. Settineri, Eui Ju Kong, Richard H. Kramer, Evan W. Miller. Voltage Imaging with a NIR-Absorbing Phosphine Oxide Rhodamine Voltage Reporter. Journal of the American Chemical Society 2021, 143 (5) , 2304-2314. https://doi.org/10.1021/jacs.0c11382
  2. Kotaro Kiyotaki, Takuto Kayukawa, Ayumi Imayoshi, Kazunori Tsubaki. Total Syntheses of FR-901235, Auxarthrones A–D, and Lamellicolic Anhydride. Organic Letters 2020, 22 (23) , 9220-9224. https://doi.org/10.1021/acs.orglett.0c03401
  3. Jingxian Fang, Lesong Li, Chu Yang, Jinping Chen, Guo-Jun Deng, Hang Gong. Tandem Oxidative Ring-Opening/Cyclization Reaction in Seconds in Open Atmosphere for the Synthesis of 1-Tetralones in Water–Acetonitrile. Organic Letters 2018, 20 (22) , 7308-7311. https://doi.org/10.1021/acs.orglett.8b03246
  4. Akane Katori, Eriko Azuma, Hina Ishimura, Kouji Kuramochi, and Kazunori Tsubaki . Fluorescent Dyes with Directly Connected Xanthone and Xanthene Units. The Journal of Organic Chemistry 2015, 80 (9) , 4603-4610. https://doi.org/10.1021/acs.joc.5b00479
  5. Luke D. Lavis and Ronald T. Raines . Bright Building Blocks for Chemical Biology. ACS Chemical Biology 2014, 9 (4) , 855-866. https://doi.org/10.1021/cb500078u
  6. Maksim V. Sednev, Christian A. Wurm, Vladimir N. Belov, and Stefan W. Hell . Carborhodol: A New Hybrid Fluorophore Obtained by Combination of Fluorescein and Carbopyronine Dye Cores. Bioconjugate Chemistry 2013, 24 (4) , 690-700. https://doi.org/10.1021/bc3006732
  7. Martha Sibrian-Vazquez, Jorge O. Escobedo, Mark Lowry, Frank R. Fronczek, and Robert M. Strongin . Field Effects Induce Bathochromic Shifts in Xanthene Dyes. Journal of the American Chemical Society 2012, 134 (25) , 10502-10508. https://doi.org/10.1021/ja302445w
  8. Shinichi Yamabe, Noriko Tsuchida, Shoko Yamazaki. A density functional theory study of the reaction mechanism of formation of phenolphthalein and fluorescein. Journal of Physical Organic Chemistry 2021, 34 (2) https://doi.org/10.1002/poc.4136
  9. Wei Chen, Ming Xian. Washington Red (WR) dyes and their imaging applications. 2020,,, 149-163. https://doi.org/10.1016/bs.mie.2020.04.027
  10. . Chemical Tools for Imaging, Manipulating, and Tracking Biological Systems: Diverse Methods Based on Optical Imaging and Fluorescence. 2020,,https://doi.org/
  11. Kazunori Tsubaki, Hikari Yamashita, Chihiro Minari, Eriko Azuma, Kouji Kuramochi, Ayumi Imayoshi. Synthesis and Optical Properties of L-Shaped Dinaphthofluoresceins with Two Peripheral Hydroxy Groups. HETEROCYCLES 2020, 101 (2) , 536. https://doi.org/10.3987/COM-19-S(F)44
  12. Aeysha Sultan, Abdul Rauf Raza, Mian Habib Ur Rehman Mehmood, Bushra Nisar, Syeda Laila Rubab, Ali Irfan, Roberto Acevedo. An Overview of Synthetic Approaches towards of Nitration of α-Tetralones. Material Science Research India 2019, 16 (3) , 189-197. https://doi.org/10.13005/msri/160301
  13. Liulin Wang, Wei Du, Zhangjun Hu, Kajsa Uvdal, Lin Li, Wei Huang. Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging. Angewandte Chemie 2019, 131 (40) , 14164-14181. https://doi.org/10.1002/ange.201901061
  14. Liulin Wang, Wei Du, Zhangjun Hu, Kajsa Uvdal, Lin Li, Wei Huang. Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging. Angewandte Chemie International Edition 2019, 58 (40) , 14026-14043. https://doi.org/10.1002/anie.201901061
  15. Naoki Ando, Hiroki Soutome, Shigehiro Yamaguchi. Near-infrared fluorescein dyes containing a tricoordinate boron atom. Chemical Science 2019, 10 (33) , 7816-7821. https://doi.org/10.1039/C9SC02314C
  16. Nadezhda S. Baleeva, Anastasia V. Khavroshechkina, Elvira R. Zaitseva, Ivan N. Myasnyanko, Marina B. Zagudaylova, Mikhail S. Baranov. Naphthalene derivatives of a conformationally locked GFP chromophore with large stokes shifts. Tetrahedron Letters 2019, 60 (34) , 150963. https://doi.org/10.1016/j.tetlet.2019.150963
  17. Xiao Luo, Jin Li, Jie Zhao, Luyan Gu, Xuhong Qian, Youjun Yang. A general approach to the design of high-performance near-infrared (NIR) D-π-A type fluorescent dyes. Chinese Chemical Letters 2019, 30 (4) , 839-846. https://doi.org/10.1016/j.cclet.2019.03.012
  18. P. V. Slitikov. Naphthophosphacyclophanes based on 1,6-dihydroxynaphthalene as bidentate ligands in the synthesis of molybdenum(0) carbonyl complexes. Russian Chemical Bulletin 2018, 67 (8) , 1500-1503. https://doi.org/10.1007/s11172-018-2246-9
  19. Ryo Hirata, Ayame Torii, Kenichi Kawano, Shiroh Futaki, Ayumi Imayoshi, Kazunori Tsubaki. Development of xanthene dyes containing arylacetylenes: The role of acetylene linker and substituents on the aryl group. Tetrahedron 2018, 74 (27) , 3608-3615. https://doi.org/10.1016/j.tet.2018.05.019
  20. Youngjun Lee. Introduction. 2018,,, 1-20. https://doi.org/10.1007/978-981-13-1645-6_1
  21. Youngjun Lee. Systematic Exploration of Indolizine-Based Small Fluorescent Molecules. 2018,,https://doi.org/10.1007/978-981-13-1645-6
  22. Qing Wang, Xiaojie Jiao, Chang Liu, Kun Huang, Song He, Liancheng Zhao, Xianshun Zeng. . Organic & Biomolecular Chemistry 2018,,, 7609. https://doi.org/10.1039/C8OB01671B
  23. Qing Wang, Kun Huang, Songtao Cai, Chang Liu, Xiaojie Jiao, Song He, Liancheng Zhao, Xianshun Zeng. . Organic & Biomolecular Chemistry 2018,,, 7163. https://doi.org/10.1039/C8OB01701H
  24. Wei Chen, Shi Xu, Jacob J. Day, Difei Wang, Ming Xian. A General Strategy for Development of Near-Infrared Fluorescent Probes for Bioimaging. Angewandte Chemie 2017, 129 (52) , 16838-16842. https://doi.org/10.1002/ange.201710688
  25. Wei Chen, Shi Xu, Jacob J. Day, Difei Wang, Ming Xian. A General Strategy for Development of Near-Infrared Fluorescent Probes for Bioimaging. Angewandte Chemie International Edition 2017, 56 (52) , 16611-16615. https://doi.org/10.1002/anie.201710688
  26. Akari Yamagami, Kenichi Kawano, Shiroh Futaki, Kouji Kuramochi, Kazunori Tsubaki. Syntheses and properties of second-generation V-shaped xanthene dyes with piperidino groups. Tetrahedron 2017, 73 (50) , 7061-7066. https://doi.org/10.1016/j.tet.2017.10.064
  27. Kengo Asai, Aiko Fukazawa, Shigehiro Yamaguchi. A Near‐Infrared Dye That Undergoes Multiple Interconversions through Acid–Base Equilibrium and Reversible Redox Processes. Angewandte Chemie 2017, 129 (24) , 6952-6956. https://doi.org/10.1002/ange.201702140
  28. Kengo Asai, Aiko Fukazawa, Shigehiro Yamaguchi. A Near‐Infrared Dye That Undergoes Multiple Interconversions through Acid–Base Equilibrium and Reversible Redox Processes. Angewandte Chemie International Edition 2017, 56 (24) , 6848-6852. https://doi.org/10.1002/anie.201702140
  29. Peter Hammershøj, Erling Thyrhaug, Pernille Harris, Pramod K. Ek, Thomas L. Andresen, Mads H. Clausen. Convenient one-step synthesis of 5-carboxy-seminaphthofluoresceins. Tetrahedron Letters 2017, 58 (16) , 1611-1615. https://doi.org/10.1016/j.tetlet.2017.03.028
  30. Aiko Fukazawa, Junichi Usuba, Raúl A. Adler, Shigehiro Yamaguchi. Synthesis of seminaphtho-phospha-fluorescein dyes based on the consecutive arylation of aryldichlorophosphines. Chemical Communications 2017, 53 (61) , 8565-8568. https://doi.org/10.1039/C7CC04323F
  31. Akane Katori, Kouji Kuramochi, Kazunori Tsubaki. Oxidative cleavage of exo-alkylidene xanthenes. Tetrahedron 2016, 72 (22) , 2997-3002. https://doi.org/10.1016/j.tet.2016.04.019
  32. Su-Young Moon, Ashlee J. Howarth, Timothy Wang, Nicolaas A. Vermeulen, Joseph T. Hupp, Omar K. Farha. A visually detectable pH responsive zirconium metal–organic framework. Chemical Communications 2016, 52 (16) , 3438-3441. https://doi.org/10.1039/C5CC10384C
  33. Xiaodong Liu, Lifen Zhang, Zhenping Cheng, Xiulin Zhu. Metal-free photoinduced electron transfer–atom transfer radical polymerization (PET–ATRP) via a visible light organic photocatalyst. Polymer Chemistry 2016, 7 (3) , 689-700. https://doi.org/10.1039/C5PY01765C
  34. Kyohei Sezukuri, Mitsuharu Suzuki, Hironobu Hayashi, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada. A laterally π-expanded fluorone dye as an efficient near infrared fluorophore. Chemical Communications 2016, 52 (27) , 4872-4875. https://doi.org/10.1039/C6CC00237D
  35. Akari Yamagami, Hina Ishimura, Akane Katori, Kouji Kuramochi, Kazunori Tsubaki. . Organic & Biomolecular Chemistry 2016,,, 10963. https://doi.org/10.1039/C6OB01967F
  36. Peter Hammershøj, E. K. Pramod Kumar, Pernille Harris, Thomas L. Andresen, Mads H. Clausen. Facile Large-Scale Synthesis of 5- and 6-Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes. European Journal of Organic Chemistry 2015, 2015 (33) , 7301-7309. https://doi.org/10.1002/ejoc.201501013
  37. Anthony Romieu. . Organic & Biomolecular Chemistry 2015,,, 1294. https://doi.org/10.1039/C4OB02076F
  38. Jiajia Yu, Huijun Zhao, Shuguang Liang, Xiaoguang Bao, Chen Zhu. . Organic & Biomolecular Chemistry 2015,,, 7924. https://doi.org/10.1039/C5OB01222H
  39. P. V. Slitikov, E. N. Rasadkina, L. K. Vasyanina, I. I. Levina, E. E. Nifant’ev. Phosphorylation of aromatic diols with phosphorous acid triamides with bulky substituents. Russian Journal of General Chemistry 2014, 84 (3) , 505-510. https://doi.org/10.1134/S1070363214030165
  40. Xiaoqing Xiong, Fengling Song, Gengwen Chen, Wen Sun, Jingyun Wang, Pan Gao, Yukang Zhang, Bo Qiao, Wenfang Li, Shiguo Sun, Jiangli Fan, Xiaojun Peng. Construction of Long-Wavelength Fluorescein Analogues and Their Application as Fluorescent Probes. Chemistry - A European Journal 2013, 19 (21) , 6538-6545. https://doi.org/10.1002/chem.201300418
  41. Eriko Azuma, Kouji Kuramochi, Kazunori Tsubaki. Alternative simple and effective synthesis of (di)benzoxanthones and their functions toward fluorescent dyes. Tetrahedron 2013, 69 (6) , 1694-1699. https://doi.org/10.1016/j.tet.2012.12.035
  42. Antje Vollrath, Stephanie Schubert, Ulrich S. Schubert. Fluorescence imaging of cancer tissue based on metal-free polymeric nanoparticles – a review. Journal of Materials Chemistry B 2013, 1 (15) , 1994. https://doi.org/10.1039/c3tb20089b

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE