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Push-pull pyropheophorbides for nonlinear optical imaging.

Anjul Khadria1, Yovan de Coene2, Przemyslaw Gawel1

  • 1Department of Chemistry, Oxford University, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. harry.anderson@chem.ox.ac.uk.

Organic & Biomolecular Chemistry
|January 6, 2017
PubMed
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This study modified pyropheophorbide-a methyl ester (PPa-OMe) dyes with electron donor/acceptor groups, enhancing nonlinear optical properties. The resulting amphiphilic dyes show increased hyperpolarizability, with potential applications in advanced imaging.

Area of Science:

  • Organic chemistry
  • Photophysics
  • Materials science

Background:

  • Pyropheophorbide-a methyl ester (PPa-OMe) derivatives are explored for tunable optical properties.
  • Modifying porphyrin-based structures with electron donor and acceptor groups is key to altering photophysical behavior.

Purpose of the Study:

  • To synthesize and characterize novel PPa-OMe derivatives with appended electron-donor and -acceptor functionalities.
  • To investigate the impact of these modifications on linear and nonlinear optical properties, including absorption, emission, and hyperpolarizability.
  • To assess the amphiphilic nature and imaging capabilities of the synthesized dyes.

Main Methods:

  • Regioselective bromination and Suzuki coupling for attaching electron-donor groups.
  • Knoevenagel condensation for introducing electron-acceptor groups.

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  • Conversion to hydrophilic bis-TEG amides to create amphiphilic dyes.
  • Spectroscopic (absorption, emission), electrochemical, TD-DFT calculations, and Hyper-Rayleigh scattering measurements.
  • Two-photon excited fluorescence (TPEF) and second harmonic generation (SHG) imaging.

    • Main Results:

    • Four PPa-OMe derivatives with varying donor/acceptor combinations were successfully synthesized.
    • Electron-donor groups significantly reduced the HOMO-LUMO gap compared to electron-acceptor groups.
    • HOMO localized on the donor, LUMO distributed on the chlorin ring and acceptor.
    • First-order hyperpolarizability increased with donor/acceptor substitution, peaking with both present.
    • TPEF and SHG imaging revealed distinct transition dipole moment orientations.

    Conclusions:

    • The strategic attachment of electron-donor and -acceptor groups effectively modulates the optical properties of PPa-OMe.
    • The synthesized amphiphilic dyes exhibit enhanced nonlinear optical responses, particularly when both donor and acceptor moieties are incorporated.
    • These findings highlight the potential of these tailored porphyrin derivatives for applications in advanced optical imaging and materials science.