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Literature DB >> 26186141

Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.

Ning Zhao¹, Sunting Xuan¹, Frank R Fronczek¹, Kevin M Smith¹, M Graça H Vicente¹.

Abstract

An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2-5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.

Entities: CellLine Chemical Disease Species

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Year: 2015 PMID： 26186141 PMCID： PMC4881425 DOI： 10.1021/acs.joc.5b01147

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

42 in total

1. Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution.

Authors: Taoufik Rohand; Mukulesh Baruah; Wenwu Qin; Noël Boens; Wim Dehaen
Journal: Chem Commun (Camb) Date: 2005-11-22 Impact factor: 6.222

2. Geometry relaxation-induced large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes.

Authors: Yinghui Chen; Jianzhang Zhao; Huimin Guo; Lijuan Xie
Journal: J Org Chem Date: 2012-02-16 Impact factor: 4.354

Review 3. BODIPY dyes in photodynamic therapy.

Authors: Anyanee Kamkaew; Siang Hui Lim; Hong Boon Lee; Lik Voon Kiew; Lip Yong Chung; Kevin Burgess
Journal: Chem Soc Rev Date: 2012-09-26 Impact factor: 54.564

4. Antenna effects in truxene-bridged BODIPY triarylzinc(II)porphyrin dyads: evidence for a dual Dexter-Förster mechanism.

Authors: Hai-Jun Xu; Antoine Bonnot; Paul-Ludovic Karsenti; Adam Langlois; Mohammed Abdelhameed; Jean-Michel Barbe; Claude P Gros; Pierre D Harvey
Journal: Dalton Trans Date: 2014-06-14 Impact factor: 4.390

5. Halogenated boron-dipyrromethenes: synthesis, properties and applications.

Authors: Vellanki Lakshmi; Malakalapalli Rajeswara Rao; Mangalampalli Ravikanth
Journal: Org Biomol Chem Date: 2015-03-07 Impact factor: 3.876

6. Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling.

Authors: Yosuke Hayashi; Shigeru Yamaguchi; Won Young Cha; Dongho Kim; Hiroshi Shinokubo
Journal: Org Lett Date: 2011-05-17 Impact factor: 6.005

7. Synthesis of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions.

Authors: Ning Zhao; M Graça H Vicente; Frank R Fronczek; Kevin M Smith
Journal: Chemistry Date: 2015-03-11 Impact factor: 5.236

8. BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine.

Authors: Li-Ya Niu; Ying-Shi Guan; Yu-Zhe Chen; Li-Zhu Wu; Chen-Ho Tung; Qing-Zheng Yang
Journal: J Am Chem Soc Date: 2012-11-08 Impact factor: 15.419

9. Slow and fast singlet energy transfers in BODIPY-gallium(III)corrole dyads linked by flexible chains.

Authors: Bertrand Brizet; Nicolas Desbois; Antoine Bonnot; Adam Langlois; Adrien Dubois; Jean-Michel Barbe; Claude P Gros; Christine Goze; Franck Denat; Pierre D Harvey
Journal: Inorg Chem Date: 2014-03-24 Impact factor: 5.165

10. Lewis acid-assisted isotopic 18F-19F exchange in BODIPY dyes: facile generation of positron emission tomography/fluorescence dual modality agents for tumor imaging.

Authors: Shuanglong Liu; Tzu-Pin Lin; Dan Li; Lauren Leamer; Hong Shan; Zibo Li; François P Gabbaï; Peter S Conti
Journal: Theranostics Date: 2013-02-21 Impact factor: 11.556

6 in total

Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.

1. Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution.

2. Geometry relaxation-induced large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes.

Review 3. BODIPY dyes in photodynamic therapy.

4. Antenna effects in truxene-bridged BODIPY triarylzinc(II)porphyrin dyads: evidence for a dual Dexter-Förster mechanism.

5. Halogenated boron-dipyrromethenes: synthesis, properties and applications.

6. Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling.

7. Synthesis of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions.

8. BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine.

9. Slow and fast singlet energy transfers in BODIPY-gallium(III)corrole dyads linked by flexible chains.

10. Lewis acid-assisted isotopic 18F-19F exchange in BODIPY dyes: facile generation of positron emission tomography/fluorescence dual modality agents for tumor imaging.

1. Synthesis and Spectroscopic Investigation of a Series of Push-Pull Boron Dipyrromethenes (BODIPYs).

2. Synthesis of BODIPY-Peptide Conjugates for Fluorescence Labeling of EGFR Overexpressing Cells.

3. Synthesis and spectroscopic properties of β,β'-dibenzo-3,5,8-triaryl-BODIPYs.

4. Enhanced Hypsochromic Shifts, Quantum Yield, and π-π Interactions in a meso,β-Heteroaryl-Fused BODIPY.

5. Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.

6. Synthesis and regioselective functionalization of perhalogenated BODIPYs.