Orthogonal Bodipy Trimers as Photosensitizers for Photodynamic Action.

Orthogonally linked BODIPY units show exceptional intersystem crossing efficiencies. We now report orthogonal BODIPY trimers with strong absorption in the visible region and high singlet oxygen generation capability. The X-ray diffraction structure confirms that the two peripheral BODIPY units are at a perpendicular angle to the core structure.

[1]  E. Akkaya,et al.  A Bifunctional Photosensitizer for Enhanced Fractional Photodynamic Therapy: Singlet Oxygen Generation in the Presence and Absence of Light. , 2016, Angewandte Chemie.

[2]  J. Roncali,et al.  BODIPY derivatives as donor materials for bulk heterojunction solar cells. , 2009, Chemical communications.

[3]  Yasuteru Urano,et al.  Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe. , 2004, Journal of the American Chemical Society.

[4]  Tugba Ozdemir,et al.  BODIPY based self-healing fluorescent gel formation via acylhydrazone linkage , 2016 .

[5]  E. Akkaya,et al.  Proof of principle for a molecular 1:2 demultiplexer to function as an autonomously switching theranostic device , 2013 .

[6]  Ruslan Guliyev,et al.  From virtual to physical: integration of chemical logic gates. , 2011, Angewandte Chemie.

[7]  E. Akkaya,et al.  Expanded bodipy dyes: anion sensing using a bodipy analog with an additional difluoroboron bridge. , 2012, Organic letters.

[8]  Jianjun He,et al.  Modified phthalocyanines for efficient near-IR sensitization of nanostructured TiO(2) electrode. , 2002, Journal of the American Chemical Society.

[9]  K. Burgess,et al.  BODIPY dyes in photodynamic therapy. , 2013, Chemical Society reviews.

[10]  Tugba Ozdemir,et al.  A near IR di-styryl BODIPY-based ratiometric fluorescent chemosensor for Hg(II) , 2010 .

[11]  W. Gallagher,et al.  A potent nonporphyrin class of photodynamic therapeutic agent: cellular localisation, cytotoxic potential and influence of hypoxia , 2005, British Journal of Cancer.

[12]  E. Akkaya,et al.  Tetrastyryl-Bodipy dyes: convenient synthesis and characterization of elusive near IR fluorophores. , 2009, Organic letters.

[13]  Seda Demirel Topel,et al.  Near IR excitation of heavy atom free Bodipy photosensitizers through the intermediacy of upconverting nanoparticles. , 2014, Chemical communications.

[14]  Y. Urano,et al.  Highly efficient and photostable photosensitizer based on BODIPY chromophore. , 2005, Journal of the American Chemical Society.

[15]  E. Akkaya,et al.  Synthesis of symmetrical multichromophoric Bodipy dyes and their facile transformation into energy transfer cassettes. , 2010, Chemistry.

[16]  E. Akkaya,et al.  Chromogenic and fluorogenic sensing of biological thiols in aqueous solutions using BODIPY-based reagents. , 2013, Organic letters.

[17]  E. Akkaya,et al.  Designing excited states: theory-guided access to efficient photosensitizers for photodynamic action. , 2011, Angewandte Chemie.

[18]  Chen-Ho Tung,et al.  BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine. , 2012, Journal of the American Chemical Society.

[19]  T. Nyokong,et al.  Synthesis, characterization and photophysical properties of an acenaphthalene fused-ring-expanded NIR absorbing aza-BODIPY dye , 2015 .

[20]  Y. Urano,et al.  Design and synthesis of a library of BODIPY-based environmental polarity sensors utilizing photoinduced electron-transfer-controlled fluorescence ON/OFF switching. , 2007, Journal of the American Chemical Society.

[21]  E. Akkaya,et al.  Heavy atom free singlet oxygen generation: doubly substituted configurations dominate S1 states of bis-BODIPYs. , 2012, The Journal of organic chemistry.

[22]  E. Akkaya,et al.  Thinking outside the silicon box: molecular and logic as an additional layer of selectivity in singlet oxygen generation for photodynamic therapy. , 2009, Journal of the American Chemical Society.

[23]  E. Akkaya,et al.  Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy. , 2006, Chemical communications.

[24]  Zijian Guo,et al.  Thienopyrrole-expanded BODIPY as a potential NIR photosensitizer for photodynamic therapy. , 2013, Chemical communications.

[25]  Lijuan Jiao,et al.  Beta-formyl-BODIPYs from the Vilsmeier-Haack reaction. , 2009, The Journal of organic chemistry.

[26]  Evan W. Miller,et al.  A selective turn-on fluorescent sensor for imaging copper in living cells. , 2006, Journal of the American Chemical Society.

[27]  Jian Xu,et al.  A water-soluble BODIPY derivative as a highly selective "Turn-On" fluorescent sensor for H2O2 sensing in vivo. , 2014, Biosensors & bioelectronics.

[28]  W. Dehaen,et al.  A highly sensitive, selective, colorimetric and near-infrared fluorescent turn-on chemosensor for Cu2+ based on BODIPY. , 2010, Chemical communications.

[29]  J. Hupp,et al.  Dye sensitized solar cells: TiO2 sensitization with a bodipy-porphyrin antenna system. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[30]  E. Akkaya,et al.  Intracellular modulation of excited-state dynamics in a chromophore dyad: differential enhancement of photocytotoxicity targeting cancer cells. , 2015, Angewandte Chemie.

[31]  K. Rurack,et al.  A Selective and Sensitive Fluoroionophore for HgII, AgI, and CuII with Virtually Decoupled Fluorophore and Receptor Units , 2000 .

[32]  Siddik Icli,et al.  A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells. , 2008, Organic letters.

[33]  A. Harriman,et al.  The chemistry of Bodipy: A new El Dorado for fluorescence tools , 2007 .

[34]  Anthony Harriman,et al.  The chemistry of fluorescent bodipy dyes: versatility unsurpassed. , 2008, Angewandte Chemie.

[35]  E. Akkaya,et al.  Fast responding and selective near-IR Bodipy dye for hydrogen sulfide sensing. , 2014, Chemical communications.

[36]  Hongbin Yan,et al.  The synthesis and crystal structure of unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene (BODIPY) , 2009 .

[37]  Shenglin Luo,et al.  A NIR heptamethine dye with intrinsic cancer targeting, imaging and photosensitizing properties. , 2012, Biomaterials.

[38]  Mohammad Khaja Nazeeruddin,et al.  Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells , 2011 .

[39]  K. Ohkubo,et al.  Charge separation in a nonfluorescent donor-acceptor dyad derived from boron dipyrromethene dye, leading to photocurrent generation. , 2005, The journal of physical chemistry. B.

[40]  Patrycja Nowak-Sliwinska,et al.  In vitro and in vivo photocytotoxicity of boron dipyrromethene derivatives for photodynamic therapy. , 2010, Journal of medicinal chemistry.

[41]  M. Zeller,et al.  Controlled Knoevenagel reactions of methyl groups of 1,3,5,7-tetramethyl BODIPY dyes for unique BODIPY dyes , 2012 .

[42]  E. Akkaya,et al.  Non-covalent functionalized SWNTs as delivery agents for novel Bodipy-based potential PDT sensitizers. , 2009, Chemical communications.

[43]  Kevin Burgess,et al.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties. , 2007, Chemical reviews.

[44]  J. Sessler,et al.  Lutetium Texaphyrin (PCI‐0123): A Near‐Infrared, Water‐Soluble Photosensitizer , 1996, Photochemistry and photobiology.

[45]  G. Ulrich,et al.  Highly substituted Bodipy dyes with spectroscopic features sensitive to the environment. , 2011, The Journal of organic chemistry.

[46]  U. Bunz,et al.  Pyridine‐Substituted BODIPY as Fluorescent Probe for Hg2+ , 2012 .

[47]  R. Thummel,et al.  Color tuning in new metal-free organic sensitizers (Bodipys) for dye-sensitized solar cells. , 2009, Chemistry.