Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

The Journal of Organic Chemistry
Adam MearesMarcin Ptaszek

Abstract

BODIPY-hydroporphyrin energy transfer arrays allow for development of a family of fluorophores featuring a common excitation band at 500 nm, tunable excitation band in the deep red/near-infrared window, and tunable emission. Their biomedical applications are contingent upon retaining their optical properties in an aqueous environment. Amphiphilic arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their optical and fluorescence properties were determined in organic solvents and aqueous surfactants. The first series of arrays contains BODIPYs with PEG substituents attached to the boron, whereas in the second series, PEG substituents are attached to the aryl at the meso positions of BODIPY. For both series of arrays, excitation of BODIPY at 500 nm results in efficient energy transfer to and bright emission of hydroporphyrin in the deep-red (640-660 nm) or near-infrared (740-760 nm) spectral windows. In aqueous solution of nonionic surfactants (Triton X-100 and Tween 20) arrays from the second series exhibit significant quenching of fluorescence, whereas properties of arrays from the first series are comparable to those observed in polar organic solvents. Reported arrays possess large effect...Continue Reading

References

May 18, 2000·The Journal of Organic Chemistry·J P StrachanJ S Lindsey
Aug 28, 2003·Journal of the American Chemical Society·Guangtao LiJürgen-Hinrich Fuhrhop
Jun 10, 2004·Chemical Reviews·Jürgen-Hinrich Fuhrhop, Tianyu Wang
Feb 15, 2005·Proceedings of the National Academy of Sciences of the United States of America·P Peter GhoroghchianMichael J Therien
Jul 2, 2005·The Journal of Organic Chemistry·Han-Je Kim, Jonathan S Lindsey
Nov 3, 2005·Journal of the American Chemical Society·P Peter GhoroghchianMichael J Therien
May 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·C K ChangJ Fajer
Aug 17, 2006·Journal of the American Chemical Society·Rakeshwar BandichhorKevin Burgess
Oct 24, 2006·Chemical Communications : Chem Comm·Serdar AtilganEngin U Akkaya
Jan 18, 2007·Bioconjugate Chemistry·Natalie A ChristianDaniel A Hammer
Oct 11, 2007·Chemical Reviews·Aurore Loudet, Kevin Burgess
Feb 15, 2008·The Journal of Organic Chemistry·Lingling LiKevin Burgess
Mar 18, 2008·The Journal of Organic Chemistry·K Eszter BorbasJonathan S Lindsey
Mar 20, 2007·Chemistry of Materials : a Publication of the American Chemical Society·P Peter GhoroghchianMichael J Therien
Apr 22, 2009·Organic Letters·Song Lin NiuAnthony Romieu
Jul 2, 2009·Journal of the American Chemical Society·Liangxing WuKevin Burgess
Jan 22, 2010·The Journal of Organic Chemistry·Michael KrayerJonathan S Lindsey
Feb 4, 2010·The Journal of Organic Chemistry·Marcin PtaszekJonathan S Lindsey
Feb 6, 2010·Journal of the American Chemical Society·Alexander NierthAndres Jäschke
Mar 24, 2010·Chemical Society Reviews·C Oliver Kappe, Erik Van der Eycken
Apr 2, 2010·ACS Applied Materials & Interfaces·Rajiv KumarParas N Prasad
Jul 22, 2010·Angewandte Chemie·Katrin KnopUlrich S Schubert
Oct 5, 2010·Bioconjugate Chemistry·Anatoliy V PopovE James Delikatny
Oct 20, 2010·Chemical Communications : Chem Comm·Raymond Ziessel, Anthony Harriman
Nov 23, 2010·Organic & Biomolecular Chemistry·Song Lin NiuAnthony Romieu
Nov 26, 2010·Journal of the American Chemical Society·Yuichiro UenoKevin Burgess
May 17, 2011·The Journal of Physical Chemistry. B·Adriana P GerolaWilker Caetano
May 24, 2011·Organic Letters·Thomas Bura, Raymond Ziessel
Sep 23, 2011·Theranostics·Tracy W B LiuGang Zheng
Nov 1, 2011·Bioconjugate Chemistry·Theresa M MawnE James Delikatny
Mar 3, 2012·The Journal of Organic Chemistry·Bertrand BrizetPierre D Harvey
Mar 23, 2012·The Journal of Physical Chemistry. a·Antoine EggenspillerShunichi Fukuzumi
May 1, 2012·Chemistry : a European Journal·Song-lin NiuRaymond Ziessel

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Citations

Jan 11, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rui LiuJonathan S Lindsey
Jan 5, 2018·Physical Chemistry Chemical Physics : PCCP·Cloé AzariasDenis Jacquemin
Aug 24, 2020·The Journal of Chemical Physics·Brian UtheMatthew Pelton

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