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Tripyrrindiones and a red-emitting fluorescent derivative

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Abstract

Orange-colored 7,8-dimethyl-2,3,12,13-tetramethoxy-(15H,17H)-tripyrrin-1,14-dione and its 2,3,7,8,12,13-hexaethyl analog were synthesized and converted to fluorescent derivatives by bridging a lactam nitrogen to the adjacent pyrrole nitrogen in a reaction with carbonyldiimidazole. The tripyrrindiones were also converted to the corresponding mono lactim methyl ethers by reaction with neat trimethylphosphite, and a corresponding difluoroboryl (BODIPY) derivative was made from the lactim by reaction with boron trifluoride etherate. X-ray structures of the tetramethoxytripyrrindione, the N,N′-carbonyl-bridged hexa-ethyltripyrrindione, and the lactim methyl ether of the hexa-ethyltripyrrindione were determined. The N,N′-bridged pigments exhibited very large Stokes’ shifts with fluorescence quantum yields ranging from 1.0 to 0.02.

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References

  1. Fischer H, Adler E (1931) Hoppe-Seyler’s Z physiol Chem 200:209

    CAS  Google Scholar 

  2. Fischer H, Reinecke H (1940) Hoppe-Seyler’s Z physiol Chem 265:9

    CAS  Google Scholar 

  3. von Dobeneck H, Schnierle F (1966) Tetrahedron Lett: 5327

  4. von Dobeneck H, Messerschmitt T, Brunner E, Winderer U (1971) Liebig’s Ann Chem 751:40

    Article  CAS  Google Scholar 

  5. Proust L (1800) Ann Chem 36:265

    Google Scholar 

  6. Simon A (1842) Anthropochemie (Berlin): 343

  7. Pane N (1916) J Am Med Assoc 66:1433

    CAS  Google Scholar 

  8. Borrien V (1917) J Pharm et Chim 16:45

    CAS  Google Scholar 

  9. Weiss M (1930) Deutsch Arch Klin Med 166:331

    CAS  Google Scholar 

  10. Berüter J, Colombo J-P, Schlunegger UP (1975) Eur J Biochem 56:239

    Article  Google Scholar 

  11. Yamaguchi T, Shioji I, Sugimoto A, Komoda Y, Nakajima H (1994) J Biochem 116:298

    CAS  Google Scholar 

  12. Falk H (1989) The chemistry of linear oligopyrroles and bile pigments. Springer, Vienna

    Google Scholar 

  13. Falk H, Müller N (1985) Org Magn Res 23:353

    CAS  Google Scholar 

  14. Roth SD, Shkindel T, Lightner DA (2007) Tetrahedron 63:11030

    Article  CAS  Google Scholar 

  15. Falk H, Neufingerl F (1979) Monatsh Chem 110:987

    Article  CAS  Google Scholar 

  16. Brower JO, Lightner DA (2002) J Org Chem 67:2713

    Article  CAS  Google Scholar 

  17. Boiadjiev SE, Lightner DA (2008) Monatsh Chem 139:503

    Article  CAS  Google Scholar 

  18. Loudet A, Burgess K (2007) Chem Rev 107:4891

    Article  CAS  Google Scholar 

  19. Falk H, Leodolter A, Schade G (1978) Monatsh Chem 109:183

    Article  CAS  Google Scholar 

  20. vos de Wael E, Pardoen JA, van Koeveringe KA, Lugtenburg J (1977) Recl Trav Chim Pays-Bas 96:306

    CAS  Google Scholar 

  21. Falk H, Gergely S, Grubmayr K, Hofer O (1977) Z Naturforsch 32b:299

    CAS  Google Scholar 

  22. Falk H, Grubmayr K, Neufingerl F (1979) Monatsh Chem 110:1127

    Article  CAS  Google Scholar 

  23. Dey SK, Lightner DA (2007) Monatsh Chem 138:687

    Article  CAS  Google Scholar 

  24. Fischer H, Hofelman H (1938) Liebig’s Ann Chem 533:216

    Article  CAS  Google Scholar 

  25. Falk H, Flödl H (1985) Monatsh Chem 116:1177

    Article  CAS  Google Scholar 

  26. Tardieux C, Bolze F, Gros CP, Guilard R (1998) Synthesis 267

  27. Falk H, Hofer O, Lehner H (1974) Monatsh Chem 105:169

    Article  CAS  Google Scholar 

  28. Datta S, Lightner DA (2008) Monatsh Chem 139:1519

    Article  CAS  Google Scholar 

  29. Huggins MT, Lightner DA (2001) Monatsh Chem 132:203

    CAS  Google Scholar 

  30. Dey SK, Lightner DA (2008) Monatsh Chem 139:1377

    Article  CAS  Google Scholar 

  31. Sheldrick GM (2003) SADABS, vers. 2.1. Bruker Analytical X-ray Systems, Madison, WI

  32. SAINT (2003) vers 6.45. Bruker Analytical X-ray Systems, Madison, WI

  33. Sheldrick GM (1997) SHELXT-L, vers. 6.14; Bruker Analytical X-ray Systems: Madison, WI

Download references

Acknowledgments

We thank the US National Institutes of Health (HD 17779) for generous support of this work, the National Science Foundation (CHE-0226402 and CHE-0521191) for providing funding for purchase of the X-ray diffractometer used in this work and for acquisition of a 400 MHz NMR spectrophotometer and upgrade of our 500 MHz NMR. We thank Dr. David Quilici and Ms. Rebekah Woolsey for the MALDI-TOF HRMS at the University of Nevada Proteomics Center (NIH P20 RR-016464 from the INBRE program of the National Center for Research.) We also thank Prof. T.W. Bell for use of the VPO apparatus.

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Authors and Affiliations

  1. Department of Chemistry, University of Nevada, Reno, NV, 89557-0216, USA

    Sanjeev K. Dey, Suchitra Datta & David A. Lightner

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  1. Sanjeev K. Dey
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  2. Suchitra Datta
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  3. David A. Lightner
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Correspondence to David A. Lightner.

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Dey, S.K., Datta, S. & Lightner, D.A. Tripyrrindiones and a red-emitting fluorescent derivative. Monatsh Chem 140, 1171–1181 (2009). https://doi.org/10.1007/s00706-009-0168-9

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  • DOI: https://doi.org/10.1007/s00706-009-0168-9

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