Corrole and Porphyrin Amino Acid Conjugates: Synthesis and Physicochemical Properties

被引:34
作者
Karikis, Kostas [1 ]
Georgilis, Evangelos [2 ,3 ]
Charalambidis, Georgios [1 ]
Petrou, Athanasia [1 ]
Vakuliuk, Olena [4 ]
Chatziioannou, Theodore [1 ]
Raptaki, Iliana [1 ]
Tsovola, Sofia [1 ]
Papakyriacou, Ioanna [2 ,3 ]
Mitraki, Anna [2 ,3 ]
Gryko, Daniel T. [4 ]
Coutsolelos, Athanassios G. [1 ]
机构
[1] Univ Crete, Dept Chem, Lab Bioinorgan Chem, Voutes Campus, Iraklion 70013, Crete, Greece
[2] Univ Crete, Dept Mat Sci & Technol, Voutes Campus, Iraklion 70013, Crete, Greece
[3] IESL FORTH, Voutes Campus, Iraklion 70013, Crete, Greece
[4] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
关键词
corroles; hydrogen bonds; phenylalanine; porphyrins; self-assembly; PHOTOINDUCED CHARGE SEPARATION; SELF-ASSEMBLING PORPHYRINS; MESOSUBSTITUTED CORROLES; PERYLENE BISIMIDE; PEPTIDE NANOTUBES; ENERGY-TRANSFER; ARRAYS; ABSORPTION; CONSTRUCTION; CHROMOPHORES;
D O I
10.1002/chem.201601026
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of conjugates of amino acids with porphyrins and corroles was synthesized. Their self-assembling ability under defined conditions was investigated by scanning electron microscopy. The morphology and photophysical properties of these molecules were studied by absorption and fluorescence spectroscopy in solid, liquid, and selfassembled forms. We observed that both corrole and porphyrin conjugated with the l-phenylalanine-L-phenylalanine peptide to form spherical nanostructures with bathochromic shifts in the emission spectra, indicating the formation of aggregates. These aggregates are characterized by the impressive absorption of light over nearly the whole visible range. The broadening of all bands was particularly strong in the case of corroles. The fluorescence lifetimes of self-assembled species were longer as compared to the solid-state form.
引用
收藏
页码:11245 / 11252
页数:8
相关论文
共 81 条
  • [1] Thermal and chemical stability of diphenylalanine peptide nanotubes: Implications for nanotechnological applications
    Adler-Abramovich, L
    Reches, M
    Sedman, VL
    Allen, S
    Tendler, SJB
    Gazit, E
    [J]. LANGMUIR, 2006, 22 (03) : 1313 - 1320
  • [2] Adler-Abramovich L, 2009, NAT NANOTECHNOL, V4, P849, DOI [10.1038/nnano.2009.298, 10.1038/NNANO.2009.298]
  • [3] [Anonymous], 2011, Angew. Chem, DOI DOI 10.1002/ANGE.201002307
  • [4] [Anonymous], 2015, ANGEW CHEM
  • [5] Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights
    Aviv, Iris
    Gross, Zeev
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) : 3995 - 4005
  • [6] Self-Organization of Polar Porphyrinoids
    Babu, Sukumaran Santhosh
    Bonifazi, Davide
    [J]. CHEMPLUSCHEM, 2014, 79 (07): : 895 - 906
  • [7] Chlorins programmed for self-assembly
    Balaban, TS
    Tamiaki, H
    Holzwarth, AR
    [J]. SUPERMOLECULAR DYE CHEMISTRY, 2005, 258 : 1 - 38
  • [8] Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal Bacteriochlorophylls c, d, and e
    Balaban, TS
    Linke-Schaetzel, M
    Bhise, AD
    Vanthuyne, N
    Roussel, C
    Anson, CE
    Buth, G
    Eichhöfer, A
    Foster, K
    Garab, G
    Gliemann, H
    Goddard, R
    Javorfi, T
    Powell, AK
    Rösner, H
    Schimmel, T
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2267 - 2275
  • [9] Green self-assembling porphyrins and chlorins as mimics of the natural bacteriochlorophylls c, d, and e
    Balaban, TS
    Linke-Schaetzel, M
    Bhise, AD
    Vanthuyne, N
    Roussel, C
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) : 3919 - 3930
  • [10] Tailoring porphyrins and chlorins for self-assembly in biomimetic artificial antenna systems
    Balaban, TS
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (08) : 612 - 623