Bodipy Dyes and Their Derivatives: Syntheses and Spectroscopic Properties

Handbook of Porphyrin ScienceHandbook of Porphyrin Science, pp. 1-164 (2010) No AccessBODIPY® Dyes and Their Derivatives: Syntheses and Spectroscopic PropertiesAurore Loudet and Kevin BurgessAurore LoudetDepartment of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842, USA and Kevin BurgessDepartment of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842, USAhttps://doi.org/10.1142/9789814307246_0009Cited by:3 PreviousNext AboutSectionsPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsRecommend to Library ShareShare onFacebookTwitterLinked InRedditEmail Abstract: The following sections are included: I. Introduction II. The BODIPY Core A. Fundamental Properties B. Syntheses of the Unsubstituted BODIPY 1 C. Syntheses of Substituted BODIPYs from Pyrroles and Acid Chlorides or Anhydrides D. From Pyrroles and Aldehydes E. From Ketopyrroles Including Syntheses of Unsymmetrical BODIPYs F. Synthesis of Symmetrical BODIPY from Pyrrole-2-Carbaldehyde III. Modifications to meso-Aromatic Substituents on the BODIPY Core A. Introduction B. Fluorescence Control via Photoinduced Electron Transfer IV. BODIPYs with Heteroatom Substituents A. From Electrophilic Substitution Reactions 1. Nitration 2. Halogenation 3. Potential for Other Electrophilic Substitution Reactions B. From Nucleophilic Attack on Halogenated BODIPYs C. From Metal Mediated C-H Functionalization D. From Nucleophilic Attack at the meso-Position V. Water-Soluble BODIPY Dyes A. From Electrophilic Substitution Reactions B. From Coupling or Substitution Reactions VI. Aryl-, Alkenyl-, Alkynyl-Substituted BODIPYs A. Meso Aryl-, Alkenyl- and Alkynyl-Substituted BODIPYs B. 3,5-Aryl-Substituted BODIPYs from Aryl-Pyrroles C. Knoevenagel Reactions with Benzaldehyde Derivatives to Give Alkenyl Systems 1. 3,5-Styryl-BODIPY Dyes 2. 1,3,5,6-Tetrastyryl-BODIPY Dyes D. From Palladium-Catalyzed Coupling Reactions at the 3- and 5-Positions VII. Energy Transfer Cassettes A. Through-Space Energy Transfer Cassettes B. Through-Bond Energy Transfer Cassettes 1. Porphyrin-Based Systems as Models of Photosynthesis 2. Polypyridine Complexes Containing Accessory BODIPY Chromophores 3. Relatively Compact Systems as Potential Probes in Biotechnology VIII. BODIPY-Based Polymers A. Poly(aryleneethynylene)s (PAEs) Co-Containing BODIPY (2,6-Positions) B. BODIPY-Based Organoboron Polymer IX. Substitution of Fluoride Atoms in the BF2-Group A. With Alkyl Groups B. With Aryl Groups C. With Alkyne Groups D. With Alkoxide Groups E. Boronium and Borenium BODIPY Cations X. Use of Metals Other Than Boron XI. BODIPY-Analogs with Extended Aromatic Conjugation A. Restricted Systems B. Extended Aromatic Systems 1. Di(iso)indomethene Dyes 2. Dyes Based on Benz[c,d]indole 3. Phenanthrene-Fused BODIPY Systems 4. Porphyrin-Fused Systems 5. Bis-BODIPYs Systems XII. Aza-BODIPY Dyes A. Tetra-Aryl Systems B. Extended Aza-BODIPY Systems 1. Restricted Systems 2. Dyes Based on Benz[c,d]indole C. Cyclized Aza-BODIPY Systems D. Other Metals XIII. Other Analogs of the BODIPYs A. GFP-Chromophore Analogs B. Fused Perylene Tetracarboxylic Diimide and BODIPY Analog C. Biimidazol-2-yl-BF2 Complexes D. Pyridine-Based Systems E. 2-Ketopyrrole Complexes F. Azobenzene Derivatives G. Miscellaneous N,N-Bidentate Diphenyl Boron Chelates H. Boryl-Substituted Thienylthiazoles XIV. Conclusion XV. References FiguresReferencesRelatedDetailsCited By 3K2S2O8 mediated synthesis of 5-aryldipyrromethanes and meso-substituted A4-tetraarylporphyrinsJoydev K. Laha and Mandeep Kaur Hunjan20 May 2021 | Journal of Porphyrins and Phthalocyanines, Vol. 25, No. 07n08Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New MethodsBruno F. O. Nascimento, Susana M. M. Lopes, Marta Pineiro and Teresa M. V. D. Pinho e Melo28 November 2019 | Molecules, Vol. 24, No. 23Fluorescent Sensing of Cesium Ions by an Amide‐Linked BODIPY Dye: Synthesis and Photophysical PropertiesEmrah Özcan and Bünyemin Çoşut20 July 2018 | ChemistrySelect, Vol. 3, No. 27 Handbook of Porphyrin ScienceMetrics History PDF download