Evidence for Interfacial Halogen Bonding

被引:34
|
作者
Swords, Wesley B. [1 ]
Simon, Sarah J. C. [2 ,3 ]
Parlane, Fraser G. L. [2 ,3 ]
Dean, Rebecca K. [2 ,3 ]
Kellett, Cameron W. [2 ,3 ]
Hu, Ke [1 ]
Meyer, Gerald J. [1 ]
Berlinguette, Curtis P. [2 ,3 ]
机构
[1] Univ N Carolina, Dept Chem, Murray Hall 2202B, Chapel Hill, NC 27599 USA
[2] Univ British Columbia, Dept Chem, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
[3] Univ British Columbia, Dept Chem & Biol Engn, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
基金
美国国家科学基金会;
关键词
dyes; halogen bonding; inorganic chemistry; semiconductor interfaces; reaction kinetics; SENSITIZED SOLAR-CELLS; ANION RECOGNITION; CHARGE RECOMBINATION; ENERGY CONVERSION; ELECTRON-TRANSFER; DYE REGENERATION; CHEMISTRY; NANOPARTICLES; SPECTROSCOPY; COMPLEXES;
D O I
10.1002/anie.201510641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A homologous series of donor--acceptor dyes was synthesized, differing only in the identity of the halogen substituents about the triphenylamine (TPA; donor) portion of each molecule. Each Dye-X (X=F, Cl, Br, and I) was immobilized on a TiO2 surface to investigate how the halogen substituents affect the reaction between the light-induced charge-separated state, TiO2(e(-))/Dye-X+, with iodide in solution. Transient absorption spectroscopy showed progressively faster reactivity towards nucleophilic iodide with more polarizable halogen substituents: Dye-F < Dye-Cl < Dye-Br < Dye-I. Given that all other structural and electronic properties for the series are held at parity, with the exception of an increasingly larger electropositive sigma-hole on the heavier halogens, the differences in dye regeneration kinetics for Dye-Cl, Dye-Br, and Dye-I are ascribed to the extent of halogen bonding with the nucleophilic solution species.
引用
收藏
页码:5956 / 5960
页数:5
相关论文
共 50 条
  • [31] Halogen bonding and chalcogen bonding mediated sensing
    Hein, Robert
    Beer, Paul D.
    CHEMICAL SCIENCE, 2022, 13 (24) : 7098 - 7125
  • [32] Halogen ... phenyl supramolecular interactions in the solid state: hydrogen versus halogen bonding and directionality
    Mooibroek, Tiddo J.
    Gamez, Patrick
    CRYSTENGCOMM, 2013, 15 (09): : 1802 - 1805
  • [33] Iodide Recognition and Sensing in Water by a Halogen-Bonding Ruthenium(II)-Based Rotaxane
    Langton, Matthew J.
    Marques, Igor
    Robinson, Sean W.
    Felix, Vitor
    Beer, Paul D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (01) : 185 - 192
  • [34] Halogen bonding: Recent advances
    Fourmigue, Marc
    CURRENT OPINION IN SOLID STATE & MATERIALS SCIENCE, 2009, 13 (3-4) : 36 - 45
  • [35] Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution
    Voelkel, Martin H. H.
    Wonner, Patrick
    Huber, Stefan Matthias
    CHEMISTRYOPEN, 2020, 9 (02) : 214 - 224
  • [36] Electrochemical Bromide Sensing with a Halogen Bonding [2]Rotaxane
    Lim, Jason Y. C.
    Beer, Paul D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (21) : 3433 - 3441
  • [37] Halogen bonding anion recognition
    Brown, Asha
    Beer, Paul D.
    CHEMICAL COMMUNICATIONS, 2016, 52 (56) : 8645 - 8658
  • [38] Electrochemical activation of halogen bonding
    Fave, Claire
    Schollhorn, Bernd
    CURRENT OPINION IN ELECTROCHEMISTRY, 2019, 15 : 89 - 96
  • [39] Alternative Motifs for Halogen Bonding
    Troff, Ralf W.
    Makela, Toni
    Topic, Filip
    Valkonen, Arto
    Raatikainen, Kari
    Rissanen, Kari
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (09) : 1617 - 1637
  • [40] Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes
    Shimizu, Karina
    da Silva, Joao Ferreira
    MOLECULES, 2018, 23 (11):