Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole-Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

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OriginalspracheEnglisch
Seiten (von - bis)14333-14355
Seitenumfang23
FachzeitschriftThe journal of organic chemistry
Jahrgang86
Ausgabenummer21
Frühes Online-Datum28 Sept. 2021
PublikationsstatusVeröffentlicht - 5 Nov. 2021

Abstract

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

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Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole-Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores. / Göbel, Dominik; Rusch, Pascal; Duvinage, Daniel et al.
in: The journal of organic chemistry, Jahrgang 86, Nr. 21, 05.11.2021, S. 14333-14355.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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title = "Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole-Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores",
abstract = "Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.",
author = "Dominik G{\"o}bel and Pascal Rusch and Daniel Duvinage and Tim Stauch and Nadja-C Bigall and Nachtsheim, {Boris J.}",
note = "Funding Information: N.-C.B. and P.R. thank the DFG for partial funding under Germany{\textquoteright}s Excellence Strategy within the Cluster of Excellence PhoenixD (EXC 2122, Project ID 390833453) and the European Research Council (ERC) under the European Union{\textquoteright}s Horizon 2020 research and innovation programme (grant agreement no. 714429).",
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language = "English",
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TY - JOUR

T1 - Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole-Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

AU - Göbel, Dominik

AU - Rusch, Pascal

AU - Duvinage, Daniel

AU - Stauch, Tim

AU - Bigall, Nadja-C

AU - Nachtsheim, Boris J.

N1 - Funding Information: N.-C.B. and P.R. thank the DFG for partial funding under Germany’s Excellence Strategy within the Cluster of Excellence PhoenixD (EXC 2122, Project ID 390833453) and the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (grant agreement no. 714429).

PY - 2021/11/5

Y1 - 2021/11/5

N2 - Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

AB - Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

UR - http://www.scopus.com/inward/record.url?scp=85117158661&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c00846

DO - 10.1021/acs.joc.1c00846

M3 - Article

VL - 86

SP - 14333

EP - 14355

JO - The journal of organic chemistry

JF - The journal of organic chemistry

SN - 0022-3263

IS - 21

ER -

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