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    Porphyrins Fused with Unactivated Polycyclic Aromatic Hydrocarbons

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    Type
    Article
    Authors
    Diev, Vyacheslav V.
    Schlenker, Cody W.
    Hanson, Kenneth
    Zhong, Qiwen
    Zimmerman, Jeramy D.
    Forrest, Stephen R.
    Thompson, Mark E.
    KAUST Grant Number
    KUS-C1-015-21
    Date
    2011-12-05
    Online Publication Date
    2011-12-05
    Print Publication Date
    2012-01-06
    Permanent link to this record
    http://hdl.handle.net/10754/599342
    
    Metadata
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    Abstract
    A systematic study of the preparation of porphyrins with extended conjugation by meso,β-fusion with polycyclic aromatic hydrocarbons (PAHs) is reported. The meso-positions of 5,15-unsubstituted porphyrins were readily functionalized with PAHs. Ring fusion using standard Scholl reaction conditions (FeCl 3, dichloromethane) occurs for perylene-substituted porphyrins to give a porphyrin β,meso annulated with perylene rings (0.7:1 ratio of syn and anti isomers). The naphthalene, pyrene, and coronene derivatives do not react under Scholl conditions but are fused using thermal cyclodehydrogenation at high temperatures, giving mixtures of syn and anti isomers of the meso,β-fused porphyrins. For pyrenyl-substituted porphyrins, a thermal method gives synthetically acceptable yields (>30%). Absorption spectra of the fused porphyrins undergo a progressive bathochromic shift in a series of naphthyl (λ max = 730 nm), coronenyl (λ max = 780 nm), pyrenyl (λ max = 815 nm), and perylenyl (λ max = 900 nm) annulated porphyrins. Despite being conjugated with unsubstituted fused PAHs, the β,meso-fused porphyrins are more soluble and processable than the parent nonfused precursors. Pyrenyl-fused porphyrins exhibit strong fluorescence in the near-infrared (NIR) spectral region, with a progressive improvement in luminescent efficiency (up to 13% with λ max = 829 nm) with increasing degree of fusion. Fused pyrenyl-porphyrins have been used as broadband absorption donor materials in photovoltaic cells, leading to devices that show comparatively high photovoltaic efficiencies. © 2011 American Chemical Society.
    Citation
    Diev VV, Schlenker CW, Hanson K, Zhong Q, Zimmerman JD, et al. (2012) Porphyrins Fused with Unactivated Polycyclic Aromatic Hydrocarbons. J Org Chem 77: 143–159. Available: http://dx.doi.org/10.1021/jo201490y.
    Sponsors
    We acknowledge Drs. Matthew Whited and Peter Djurovich for helpful discussion. The Department of Energy, Office of Basic Energy Sciences as part of Energy Frontier Research Center program, the Center for Energy Nanoscience (DE-SC0001013) are acknowledged for support of the OPV studies of compound 2d (C.W.S. and J.D.Z.). We also acknowledge the NSF SOLAR program (Award ID 0934098, S.R.F and Q.Z.), Universal Display Corporation, Global Photonic Energy Corporation and the Center for Advanced Molecular Photovoltaics (CAMP) (KUS-C1-015-21) of the King Abdullah University of Science and Technology (KAUST) for financial support of the other science presented here.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/jo201490y
    PubMed ID
    22077105
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo201490y
    Scopus Count
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