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 › peer-review

9 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

Keywords

Acetamide
ESIPT
Fluorescence
Phthalimide
Sulfonamide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

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 (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.",

keywords = "Acetamide, ESIPT, Fluorescence, Phthalimide, Sulfonamide",

author = "Hideki Okamoto and Kazumasa Itani and Minoru Yamaji and Hiroyuki Konishi and Hiromi Ota",

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T1 - Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state

AU - Okamoto, Hideki

AU - Itani, Kazumasa

AU - Yamaji, Minoru

AU - Konishi, Hiroyuki

AU - Ota, Hiromi

PY - 2018/1/24

Y1 - 2018/1/24

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 (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.

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 (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.

KW - Acetamide

KW - ESIPT

KW - Fluorescence

KW - Phthalimide

KW - Sulfonamide

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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

Abstract

Keywords

ASJC Scopus subject areas

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