Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state

• Published in: Tetrahedron letters Vol. 59; no. 4; pp. 388 - 391
• Main Authors: Okamoto, Hideki, Itani, Kazumasa, Yamaji, Minoru, Konishi, Hiroyuki, Ota, Hiromi
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 24.01.2018
• Subjects: Acetamide; ESIPT; Fluorescence; Phthalimide; Sulfonamide; Fluorescence; Phthalimide; Sulfonamide; Acetamide; ESIPT
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.12.049

[Display omitted] •3-Amido-substituted phthalimides display red-shifted fluorescence via ESIPT process.•The ESIPT fluorescence features were qualitatively explained by (TD) DFT calculations.•Amido-substituted phthalimides emit RGBY fluorescence in the solid state.•Tf-amidophthalimides shows efficient ESIPT emission ΦF = 0.50 in the solid state. Fluorescence properties of phthalimide derivatives (1) incorporating sulfonamide and acetamide functionalities at the 3-position were investigated both in solution and in the solid states to reveal the effects of the amide functionalities on the fluorescence properties. In the solid state, sulfonamides 1a and 1b, respectively, gave off red (λFmax 595 nm) and green (λFmax 537 nm) emission through an ESIPT process. Acetamides 1c and 1d, respectively displayed blue (λFmax 432 nm) and yellow (λFmax 560 nm) emission. Through simply modifying the amide functionality, phthalimide 1 displayed multicolor RGBY emission in the solid state.