L., The Convergence of Synthetic Organic and Polymer Chemistries.

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R., Two enabling architectures for DNA-templated organic synthesis.

One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Terminal Acetylenes and Generated Azides.

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The simple and the complex in organic synthesis.

(2018) Computational Studies of Noncovalent Interactions in Ligand-Gated Ion Channels – and - Synthesis and Characterization of Red and Near Infrared Cyanine Dyes. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9XK8CQF.

L., Facile syntheses of surface-functionalized micelles and shell cross-linked nanoparticles.

8. Bouteiller C, Clave G, Bernardin A, Chipon B, Massonneau M, Renard P-Y. . Novel Water-Soluble Near-Infrared Cyanine Dyes: Synthesis, Spectral Properties, and Use in the Preparation of Internally Quenched Fluorescent Probes. 2007;18:1303-17

Synthesis of Cyanine Dyes | SpringerLink

We developed a versatile synthetic approach for cyanine polyelectrolytes consisting of an anionic sulfoethyl methacrylate / methacrylate backbone and either pentamethine or trimethine cationic cyanine counter ions with contents up to 50% of polymer repeating units. The synthesis route consists of a thermal radical copolymerization, followed by deprotonation of the sulfoethyl group and a salt metathesis reaction to incorporation the dyes. The cyanine polyelectrolytes showed a strongly decreased solubility in chlorinated solvents, which allowed the fabrication of the first solution-processed regular cyanine bilayer solar cells.

Among the cyanine dyes evaluated, compound 3 (IR783), the polymethine cyanine-based dye with the indolenine nucleus, a chlorinated cyclohexenyl center and a sulfonate group, was found to be the best candidate for NIR fluorescence tumor imaging in the series of NIRFs 1-5, 7-10, Cypate (6), ICG and IR820 probed for their absorbance/fluorescence properties. Although, NIRF 3 was the best both in terms of the spectral properties and tumor affinity, it would not be feasible to use it in the original form for our purposes. It needed further functionalization before conjugation to HPPH (3-(1'-hexyloxyethyl)pyropheophorbide-a), a highly effective photosensitizer undergoing Phase II human clinical trials []. In addition, cyanine dyes 5, 7-10 were synthesized from their parent IR820 and 3 (IR783) by replacing the central chlorinated cyclohexenyl group with 3-mercaptobenzoic acid (to yield 7 and 10), 4-mercaptobenzoic acid (to yield 5) and 4-aminophenol (to yield 8 and 9). Also, among the functionalized NIRFs (5, 7-10), the best structural substitute in terms of tumor uptake was found to be 4-aminothiophenol. At the same time, the photophysical data showed that the substitution with 4-aminothiophenol caused quenching of the fluorescence in substituted NIRFs 8 and 9. Based on the results reported in this study, further studies were performed: the NIRFs 5, 7, 8, 9 and 10 were conjugated with HPPH in the mono and di-forms. See the succeeding paper (Part-2, pages 703 - 718). NIRFs 5 and 7 were used to assess whether the position of the dye with respect to HPPH within the conjugate made a difference in PDT response.

EP1112254A2 - Cyanine dyes and synthesis methods …

Finally, three appendices are presented. Appendix A describes early work to synthesize and characterize a -hydroxy substituted Cy5 dye. Appendix B offers many of the same computations as Chapters 2 and 3 using HF instead of DFT. Appendix C describes orbital mixing of cyanine dyes from Chapter 5 using HF instead of DFT.

16. Narayanan N, Patonay G. A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels. 1995;60:2391-5 doi:10.1021/jo00113a018

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  • Synthesis of Cyanine Dyes - ResearchGate

    A.; Ham, J., Synthesis of Functionalized Organotrifluoroborates via the 1,3-Dipolar Cycloaddition of Azides.

  • Microwave synthesis of cyanine dyes

    L., Organocatalytic polymerization of ethylene oxide and the controlled synthesis of peo-based hydrogel networks.

  • Cyanine dyes and synthesis methods thereof - …

    M., Preparation of alumina supported copper nanoparticles and their application in the synthesis of 1,2,3-triazoles.

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Cyanine dyes and synthesis methods thereof Abstract

Chapter 5 describes the synthesis and characterization of a series of -aromatic-acetylene cyanine dyes which feature a very large Stokes shift. Synthesis of the dyes features a key Sonagashira reaction. These dyes are investigated photophysically and computationally using time dependent DFT (TDDFT). The mechanism for this Stokes shift is an excitation to the S2 state, relaxation to the S1 state, and normal cyanine fluorescence.

Synthesis and Validation of Cyanine-Based Dyes for …

Franca Bigi was born in Parma, Italy, in 1955. She received her laurea degree (cum laude) in chemistry from the University of Parma in 1979. After a two-year fellowship at Accademia Nazionale dei Lincei, from 1983 to 1992 she had a permanent position as Researcher at Parma University in the group of Professor G. Casnati. In 1992, she was promoted to Associate Professor of Organic Chemistry at the Faculty of Science of the Parma University. Her research interests concern the development of selective and environmentally friendly procedures under heterogeneous catalysis for fine chemicals synthesis. More recently, she has been interested in the preparation of chiral organic−inorganic hybrid materials to promote stereoselective processes, and she has developed uncatalyzed Knöevenagel condensations in water.

Synthesis and Characterization of Heptamethine Cyanine Dyes

Raimondo Maggi was born in Parma, Italy, in 1963. He graduated from the University of Parma in 1989 (working with Prof. Giuseppe Casnati), and he received his Ph.D. in organic chemistry (under the direction of Prof. Giovanni Sartori) from the same University in 1992. In 1995, he carried out his postdoctoral research with Prof. Manfred Schlosser at the Lausanne University. He began his career at the University of Parma in 1997 as Researcher, and in 2002 he was promoted to Associate Professor of Organic Chemistry. His research interests include the preparation and use of heterogeneous (chiral) catalysts for the environmentally friendly synthesis of fine chemicals and pharmaceuticals. He has published about 80 original studies.

"Unsymmetrical Trimethine Cyanine Dyes: Synthesis, …

Roberto Ballini received an S.B. degree in chemistry from the University of Camerino, Italy. After an experience in the petrochemical industry (ENI-ANIC, Ravenna), he began his academic career in 1975 at the University of Camerino as a Research Fellow. He became Assistant Professor in 1978, was promoted to Associate Professor of Organic Chemistry, and then to full Professor (organic chemistry) in 2000. His recent research interests include the chemistry of aliphatic nitrocompounds, the formation and cleavage of C−C bonds, the studies and application of heterogeneous catalysis, the synthesis of natural products, and the use of aqueous media in organic reactions.

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