Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes

Aleksey A. Vasilev, Chen Li, Klaus Müllen, Kurt De Mey, I. Asselberghs, K. Clays, B. Champagne, S.E. Angelova, M.I. Spassova

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    Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)- ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (β up to 1300 ± 50 × 10 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.
    Original languageEnglish
    Pages (from-to)22711-22719
    Number of pages9
    JournalJournal of Physical Chemistry C: Nanomaterials and interfaces
    Issue number43
    Publication statusPublished - 1 Nov 2012


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