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

Hideki Okamoto; Kazumasa Itani; Minoru Yamaji; Hiroyuki Konishi; Hiromi Ota

doi:10.1016/j.tetlet.2017.12.049

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

Hideki Okamoto, Kazumasa Itani, Minoru Yamaji, Hiroyuki Konishi, Hiromi Ota

Research output: Contribution to journal › Article

5 Citations (Scopus)

Abstract

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 (λ^F _max 595 nm) and green (λ^F _max 537 nm) emission through an ESIPT process. Acetamides 1c and 1d, respectively displayed blue (λ^F _max 432 nm) and yellow (λ^F _max 560 nm) emission. Through simply modifying the amide functionality, phthalimide 1 displayed multicolor RGBY emission in the solid state.

Original language	English
Pages (from-to)	388-391
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2017.12.049
Publication status	Published - Jan 24 2018

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Keywords

Acetamide
ESIPT
Fluorescence
Phthalimide
Sulfonamide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Okamoto, H., Itani, K., Yamaji, M., Konishi, H., & Ota, H. (2018). Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state. Tetrahedron Letters, 59(4), 388-391. https://doi.org/10.1016/j.tetlet.2017.12.049

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AU - Okamoto, Hideki

AU - Itani, Kazumasa

AU - Yamaji, Minoru

AU - Konishi, Hiroyuki

AU - Ota, Hiromi

PY - 2018/1/24

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N2 - 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 (λF max 595 nm) and green (λF max 537 nm) emission through an ESIPT process. Acetamides 1c and 1d, respectively displayed blue (λF max 432 nm) and yellow (λF max 560 nm) emission. Through simply modifying the amide functionality, phthalimide 1 displayed multicolor RGBY emission in the solid state.

AB - 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 (λF max 595 nm) and green (λF max 537 nm) emission through an ESIPT process. Acetamides 1c and 1d, respectively displayed blue (λF max 432 nm) and yellow (λF max 560 nm) emission. Through simply modifying the amide functionality, phthalimide 1 displayed multicolor RGBY emission in the solid state.

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10.1016/j.tetlet.2017.12.049