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 journalArticle

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 - 2010 Dec 17

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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