4.6 Article

Effective Tuning of Ketocyanine Derivatives through Acceptor Substitution

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 21, Pages 7721-7725

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406625

Keywords

cyanine dyes; donor-acceptor systems; optical properties; structure-activity relationships

Funding

  1. National Science Foundation of the NSF [CHE-1307118]
  2. BES of Department of Energy [DE-SC0001087]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1307118] Funding Source: National Science Foundation

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A series of ketocyanine derivatives possessing bis(diarylamino)fluorenyl donors and variable acceptors installed at the bridging carbon atom were synthesized to investigate how the electronic structure of the dye can be systemically tuned through stabilization of the cyanine-like character of the donor by increasing the acceptor strength. Analysis of the (HNMR)-H-1 spectra indicates that the charge-separated species dominates in these dyes, given that carbons possessing a positive or negative charge in the resonance structures of this state purposefully shift downfield or upfield, respectively, depending on the strength of the acceptor moiety. In DAA-Fl-PI, the acceptor strength and the gain of acceptor aromaticity indicates a predisposition of the separated state, indicated by asymmetry in the (HNMR)-H-1 spectrum, as well as uneven distribution of the HOMO on the fluorenyl donor.

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