Synthesis of Near-Infrared Light-responsive Dyes Based on N-Confused Porphyrinoids

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  • Ishida Masatoshi
    Department of Applied Chemistry, Graduate School of Engineering, Kyushu University

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  • N-混乱修飾法による近赤外光応答性ポルフィリン類縁色素の合成
  • N-コンラン シュウショクホウ ニ ヨル キン セキガイコウ オウトウセイ ポルフィリン ルイエン シキソ ノ ゴウセイ

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Abstract

<p>Recently, optical imaging technology in the second near-infrared (NIR-II, λ =1000—1400 nm) window has attracted attention due to the merits of high S/N ratio as well as real-time detection at deeper penetration in biological tissues compared to the light energy in the traditionally-used visible and first near-infrared window (NIR-I, λ=700—1000 nm) regions. As potential small organic NIR-II chromophores, various polymethines and phthalocyanine-based dyes have shown superior biocompatibility, structure designability, and optical wavelength tunability. However, dye instability arising from the small HOMO-LUMO band gap is a common technical drawback that limits the scope of current applications.</p><p>In this regard, porphyrins and their analogues could be potential NIR chromophore scaffolds offering new opportunities for optical materials to be used in the fields ranging from light-harvesting to sensing and therapeutic applications. Several skeletal modifications of the porphyrins, such as 1) core expansion, 2) peripheral fusion, and 3) chromophore array, could downshift the wavelength to the NIR-II window along with high photo- and chemical stability. This article describes the synthesis of a series of large π-conjugated “N-confused” porphyrin analogues with inverted pyrrole rings linked at the α and β-positions as key structures to furnish the desired optical properties in the use of optical applications. Furthermore, metal complexation-induced molecular orbital mixing/tuning of the macrocyclic porphyrin scaffolds enabled the fundamental optical and excited-state dynamics.</p>

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