Fully Functionalizable β,β′-BODIPY Dimer: Synthesis, Structure, and Photophysical Signatures

被引:22
作者
Arroyo-Cordoba, Ismael J. [1 ]
Sola-Llano, Rebeca [2 ]
Epelde-Elezcano, Nerea [2 ]
Lopez Arbeloa, Inigo [2 ]
Martinez-Martinez, Virginia [2 ]
Pena-Cabrera, Eduardo [1 ]
机构
[1] Univ Guanajuato, Dept Quim, Noria Alta S-N, Guanajuato 36050, Mexico
[2] Univ Pais Vasco EHU, Dept Quim Fis, Apartado 644, Bilbao 48080, Spain
关键词
SINGLET OXYGEN GENERATION; BORON-DIPYRROMETHENE DYES; BODIPY DYES; SPECTROSCOPIC PROPERTIES; LASER-EMISSION; CHEMISTRY; PHOTOSENSITIZERS; FLUORESCENCE; DERIVATIVES; DESIGN;
D O I
10.1021/acs.joc.8b01429
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The versatility in the synthesis of BODIPY derivatives in terms of functionalization is further demonstrated. In particular, in this work beta-beta'-BODIPY dimers with varied functional groups in the meso positions were synthesized in very efficient yields and short reaction times from a single platform. A photophysical study was carried out in all of the compounds. The resultant dimers show absorption bands at around 600 nm as a consequence of electronically coupled monomers disposed with a dihedral angle of around 30 degrees, which is supported by theoretical simulations. The emission properties of these molecules are distinguished by the appearance of an ICT state as the polarity of the solvent increases.
引用
收藏
页码:10186 / 10196
页数:11
相关论文
共 40 条
  • [1] A versatile synthetic approach to design tailor-made push-pull chromophores with intriguing and tunable photophysical signatures
    Belmonte-Vazquez, Jose L.
    Sola-Llano, Rebeca
    Banuelos, Jorge
    Betancourt-Mendiola, Lourdes
    Vazquez-Guevara, Miguel A.
    Lopez-Arbeloa, Inigo
    Pena-Cabrera, Eduardo
    [J]. DYES AND PIGMENTS, 2017, 147 : 246 - 259
  • [2] Lighting the way ahead with boron dipyrromethene (Bodipy) dyes
    Benniston, Andrew C.
    Copley, Graeme
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (21) : 4124 - 4131
  • [3] Scope and Limitations of the Liebeskind-Srogl Cross-Coupling Reactions Involving the Biellmann BODIPY
    Betancourt-Mendiola, Lourdes
    Valois-Escamilla, Ismael
    Arbeloa, Teresa
    Banuelos, Jorge
    Lopez Arbeloa, Inigo
    Flores-Rizo, Juan O.
    Hu, Rongrong
    Lager, Erik
    Gomez-Duran, Cesar F. A.
    Belmonte-Vazquez, Jose L.
    Martinez-Gonzalez, Mayra R.
    Arroyo, Ismael J.
    Osorio-Martinez, Carlos A.
    Alvarado-Martinez, Enrique
    Urias-Benavides, Arlette
    Gutierrez-Ramos, Brenda D.
    Tang, Ben Zhong
    Pena-Cabrera, Eduardo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) : 5771 - 5782
  • [4] Curcumin "Drug" Stabilized in Oxidovanadium(IV)-BODIPY Conjugates for Mitochondria-Targeted Photocytotoxicity
    Bhattacharyya, Utso
    Kumar, Brijesh
    Garai, Aditya
    Bhattacharyya, Arnab
    Kumar, Arun
    Banerjee, Samya
    Kondaiah, Paturu
    Chakravarty, Akhil R.
    [J]. INORGANIC CHEMISTRY, 2017, 56 (20) : 12457 - 12468
  • [5] Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy
    Boens, Noel
    Verbelen, Bram
    Dehaen, Wim
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (30) : 6577 - 6595
  • [6] Bis(BF2)-2,2′-bidipyrrins (BisBODIPYs):: Highly fluorescent BODIPY dimers with large Stokes shifts
    Broering, Martin
    Krueger, Robin
    Link, Stephan
    Kleeberg, Christian
    Koehler, Silke
    Xie, Xiulian
    Ventura, Barbara
    Flamigni, Lucia
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (10) : 2976 - 2983
  • [7] Axially Chiral BODIPY DYEmers: An Apparent Exception to the Exciton Chirality Rule
    Bruhn, Torsten
    Pescitelli, Gennaro
    Jurinovich, Sandro
    Schaumloeffel, Anu
    Witterauf, Franziska
    Ahrens, Johannes
    Broering, Martin
    Bringmann, Gerhard
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14592 - 14595
  • [8] Tetrastyryl-Bodipy Dyes: Convenient Synthesis and Characterization of Elusive Near IR Fluorophores
    Buyukcakir, Onur
    Bozdemir, O. Altan
    Kolemen, Safacan
    Erbas, Sundus
    Akkaya, Engin U.
    [J]. ORGANIC LETTERS, 2009, 11 (20) : 4644 - 4647
  • [9] Designing Excited States: Theory-Guided Access to Efficient Photosensitizers for Photodynamic Action
    Cakmak, Yusuf
    Kolemen, Safacan
    Duman, Selin
    Dede, Yavuz
    Dolen, Yusuf
    Kilic, Bilal
    Kostereli, Ziya
    Yildirim, Leyla Tatar
    Dogan, A. Lale
    Guc, Dicle
    Akkaya, Engin U.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 11937 - 11941
  • [10] 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations
    Chen, J
    Burghart, A
    Derecskei-Kovacs, A
    Burgess, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 2900 - 2906