Literature DB >> 27251595

Synthesis and regioselective functionalization of perhalogenated BODIPYs.

Ning Zhao1, Sunting Xuan, Brandon Byrd, Frank R Fronczek, Kevin M Smith, M Graça H Vicente.   

Abstract

Three perhalogenated BODIPYs (1b-3b), bearing chloro and bromo groups at all carbon positions, were synthesized and characterized. The reactivity of BODIPY 3b was investigated under Stille cross-coupling reactions, and single crystal X-ray analysis was used to confirm the regioselectivity of the reactions. Further substitution at the boron atom produced nona-functionalized BODIPYs 7a,b, which show 676 and 739 nm emissions with 91 and 100 nm Stokes shifts, respectively.

Entities:  

Year:  2016        PMID： 27251595      PMCID： PMC4927422          DOI： 10.1039/c6ob00935b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  36 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

3.  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

4.  Long wavelength red fluorescent dyes from 3,5-diiodo-BODIPYs.

Authors:  Lijuan Jiao; Changjiang Yu; Timsy Uppal; Mingming Liu; Yan Li; Yunyou Zhou; Erhong Hao; Xiaoke Hu; M Graça H Vicente
Journal:  Org Biomol Chem       Date:  2010-04-14       Impact factor: 3.876

5.  Manipulating non-innocent π-spacers: the challenges of using 2,6-disubstituted BODIPY cores within donor-acceptor light-harvesting motifs.

Authors:  Catherine Bonnier; Devin D Machin; Omar Abdi; Bryan D Koivisto
Journal:  Org Biomol Chem       Date:  2013-06-14       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.  The fluorescent probe Bodipy-FL-verapamil is a substrate for both P-glycoprotein and multidrug resistance-related protein (MRP)-1.

Authors:  Enrico Crivellato; Luigi Candussio; Anna M Rosati; Fiora Bartoli-Klugmann; Franco Mallardi; Giuliana Decorti
Journal:  J Histochem Cytochem       Date:  2002-05       Impact factor: 2.479

8.  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

9.  Synthesis and in Vitro Studies of a Series of Carborane-Containing Boron Dipyrromethenes (BODIPYs).

Authors:  Sunting Xuan; Ning Zhao; Zehua Zhou; Frank R Fronczek; M Graça H Vicente
Journal:  J Med Chem       Date:  2016-02-17       Impact factor: 7.446

10.  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
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  5 in total

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

Authors:  Sunting Xuan; Ning Zhao; Xiangyi Ke; Zehua Zhou; Frank R Fronczek; Karl M Kadish; Kevin M Smith; M Graça H Vicente
Journal:  J Org Chem       Date:  2017-02-16       Impact factor: 4.354

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

Authors:  Ning Zhao; Tyrslai M Williams; Zehua Zhou; Frank R Fronczek; Martha Sibrian-Vazquez; Seetharama D Jois; M Graça H Vicente
Journal:  Bioconjug Chem       Date:  2017-04-28       Impact factor: 4.774

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

Authors:  Ning Zhao; Sunting Xuan; Frank R Fronczek; Kevin M Smith; M Graça H Vicente
Journal:  J Org Chem       Date:  2017-03-10       Impact factor: 4.354

4.  Development of a multi faceted platform containing a tetrazine, fluorophore and chelator: synthesis, characterization, radiolabeling, and immuno-SPECT imaging.

Authors:  Anthony W McDonagh; Brooke L McNeil; Julie Rousseau; Ryan J Roberts; Helen Merkens; Hua Yang; François Bénard; Caterina F Ramogida
Journal:  EJNMMI Radiopharm Chem       Date:  2022-06-06

5.  Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron.

Authors:  Maodie Wang; M Graça H Vicente; Deanna Mason; Petia Bobadova-Parvanova
Journal:  ACS Omega       Date:  2018-05-21
  5 in total

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