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 journalArticle

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 (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.

Original languageEnglish
Pages (from-to)388-391
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number4
DOIs
Publication statusPublished - Jan 24 2018

Fingerprint

Proton transfer
Sulfonamides
Excited states
Amides
Protons
Acetamides
Fluorescence
Derivatives
phthalimide
acetamide

Keywords

  • Acetamide
  • ESIPT
  • Fluorescence
  • Phthalimide
  • Sulfonamide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state. / Okamoto, Hideki; Itani, Kazumasa; Yamaji, Minoru; Konishi, Hiroyuki; Ota, Hiromi.

In: Tetrahedron Letters, Vol. 59, No. 4, 24.01.2018, p. 388-391.

Research output: Contribution to journalArticle

Okamoto, Hideki ; Itani, Kazumasa ; Yamaji, Minoru ; Konishi, Hiroyuki ; Ota, Hiromi. / Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 4. pp. 388-391.
@article{3ec0299a45694009844cdd29b9688cfc,
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 (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.",
keywords = "Acetamide, ESIPT, Fluorescence, Phthalimide, Sulfonamide",
author = "Hideki Okamoto and Kazumasa Itani and Minoru Yamaji and Hiroyuki Konishi and Hiromi Ota",
year = "2018",
month = "1",
day = "24",
doi = "10.1016/j.tetlet.2017.12.049",
language = "English",
volume = "59",
pages = "388--391",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

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 (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.

KW - Acetamide

KW - ESIPT

KW - Fluorescence

KW - Phthalimide

KW - Sulfonamide

UR - http://www.scopus.com/inward/record.url?scp=85038365103&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85038365103&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.12.049

DO - 10.1016/j.tetlet.2017.12.049

M3 - Article

AN - SCOPUS:85038365103

VL - 59

SP - 388

EP - 391

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -