A Tunable, Fullerene-Based Molecular Amplifier for Vibrational Circular Dichroism

被引:5
作者
Strudwick, Benjamin H. [1 ]
Koenis, Mark A. J. [1 ]
Sanders, Hans J. [1 ]
Nicu, Valentin P. [2 ]
Woutersen, Sander [1 ]
Buma, Wybren Jan [1 ]
机构
[1] Univ Amsterdam, Mol Photon Grp, Vant Hoff Inst Mol Sci, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands
[2] Lucian Blaga Univ Sibiu, Dept Environm Sci Phys Phys Educ & Sport, Ioan Ratiu St 7-9, Sibiu 550012, Romania
关键词
chirality; density functional calculations; fullerenes; spectroelectrochemistry; vibrational circular dichroism; DENSITY-FUNCTIONAL THEORY; ELECTROCHEMICAL DETECTION; SUPRAMOLECULAR CHIRALITY; OPTICAL-ACTIVITY; PROBE; CONFORMATION; ABSORPTION; SPECTRA; EPR;
D O I
10.1002/chem.201902190
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Vibrational circular dichroism (VCD) studies are reported on a chiral compound in which a fullerene C-60 moiety is used as an electron acceptor and local VCD amplifier for an alanine-based peptide chain. Four redox states are investigated in this study, of which three are reduced species that possess low-lying electronic states as confirmed by UV/Vis spectroelectrochemistry. VCD measurements in combination with (TD)DFT calculations are used to investigate (i) how the low-lying electronic states of the reduced species modulate the amplification of VCD signals, (ii) how this amplification depends on the distance between oscillator and amplifier, and (iii) how the spatial extent of the amplifier influences amplification. These results pave the way for further development of tailored molecular VCD amplifiers.
引用
收藏
页码:12560 / 12566
页数:7
相关论文
共 50 条
  • [1] [Anonymous], 1971, The Theory of Optical Activity
  • [2] [Anonymous], ANGEW CHEM
  • [3] Electronic properties of charged fullerenes characterized by EPR and Vis-NIR spectroscopy
    Baumgarten, M
    Gherghel, L
    [J]. APPLIED MAGNETIC RESONANCE, 1996, 11 (02) : 171 - 182
  • [4] EPR AND OPTICAL-ABSORPTION SPECTRA OF REDUCED BUCKMINSTERFULLERENE
    BAUMGARTEN, M
    GUGEL, A
    GHERGHEL, L
    [J]. ADVANCED MATERIALS, 1993, 5 (06) : 458 - 461
  • [5] VELOCITY-DEPENDENT PROPERTY SURFACES AND THE THEORY OF VIBRATIONAL CIRCULAR-DICHROISM
    BUCKINGHAM, AD
    FOWLER, PW
    GALWAS, PA
    [J]. CHEMICAL PHYSICS, 1987, 112 (01) : 1 - 14
  • [6] Chirality and Diastereoselection of Δ/Λ-Configured Tetrahedral Zinc Complexes through Enantiopure Schiff Base Complexes: Combined Vibrational Circular Dichroism, Density Functional Theory, 1H NMR, and X-ray Structural Studies
    Chamayou, Anne-Christine
    Luedeke, Steffen
    Brecht, Volker
    Freedman, Teresa B.
    Nafie, Laurence A.
    Janiak, Christoph
    [J]. INORGANIC CHEMISTRY, 2011, 50 (22) : 11363 - 11374
  • [7] Vibrational Circular Dichroism versus Optical Rotation Dispersion and Electronic Circular Dichroism for diastereomers: the stereochemistry of 3-(1′-hydroxyethyl)-1-(3′-phenylpropanoyl)-azetidin-2-one
    De Gussem, Ewoud
    Bultinck, Patrick
    Feledziak, Marion
    Marchand-Brynaert, Jacqueline
    Stevens, Christian V.
    Herrebout, Wouter
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2012, 14 (24) : 8562 - 8571
  • [8] Prediction of vibrational circular dichroism spectra using density functional theory: Camphor and fenchone
    Devlin, FJ
    Stephens, PJ
    Cheeseman, JR
    Frisch, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) : 6327 - 6328
  • [9] SYNTHESES, STRUCTURES, AND PROPERTIES OF METHANOFULLERENES
    DIEDERICH, F
    ISAACS, L
    PHILP, D
    [J]. CHEMICAL SOCIETY REVIEWS, 1994, 23 (04) : 243 - 255
  • [10] Elucidating the Structure of Chiral Molecules by using Amplified Vibrational Circular Dichroism: From Theory to Experimental Realization
    Domingos, Sergio R.
    Hartl, Frantisek
    Buma, Wybren Jan
    Woutersen, Sander
    [J]. CHEMPHYSCHEM, 2015, 16 (16) : 3363 - 3373