Synthesis and photophysical properties of N-fused tetraphenylporphyrin derivatives: Near-infrared organic dye of [18]annulenic compounds

Shinya Ikeda, Motoki Toganoh, Shanmugam Easwaramoorthi, Jong Min Lim, Dongho Kim, Hiroyuki Furuta

    Research output: Contribution to journalArticlepeer-review

    37 Citations (Scopus)

    Abstract

    A variety of N-fused porphyrin derivatives were prepared and their photophysical properties were investigated. Although intact N-fused tetraarylporphyrins showed almost no emission, introduction of electron-withdrawing groups such as a nitro group and a cyano group on the macrocycles caused significant refinements in their emission efficiency. Long emission wavelengths (900-1000 nm) as well as fairly large Stokes shifts (∼1200 cm-1) are exceptionally unique photophysical properties among [18]annulenic compounds, which could be rationalized by the excited state intramolecular proton transfer (ESIPT) process. Relatively weak emission quantum yields (∼5.0 × 10-4) and unusually short S1 state lifetimes (∼13.5 ps) are in good agreement with the ESIPT process. The solvent and substituent effects on the photophysical properties are also discussed in conjunction with the theoretical studies, where the mesityl groups at the meso-positions play a unique role.

    Original languageEnglish
    Pages (from-to)8637-8649
    Number of pages13
    JournalJournal of Organic Chemistry
    Volume75
    Issue number24
    DOIs
    Publication statusPublished - Dec 17 2010

    All Science Journal Classification (ASJC) codes

    • Organic Chemistry

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