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Title: Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride

A microcrystalline carboxyl-functionalized imidazolium chloride, namely 1-carboxymethyl-3-ethylimidazolium chloride, C 7H 11N 2O 2 +·Cl , has been synthesized and characterized by elemental analysis, attenuated total reflectance Fourier transform IR spectroscopy (ATR-FT-IR), single-crystal X-ray diffraction, thermal analysis (TGA/DSC), and photoluminescence spectroscopy. In the crystal structure, cations and anions are linked by C—H...Cl and C—H...O hydrogen bonds to create a helix along the [010] direction. Adjacent helical chains are further interconnected through O—H...Cl and C—H...O hydrogen bonds to form a (101¯) layer. Finally, neighboring layers are joined together via C—H...Cl contacts to generate a three-dimensional supramolecular architecture. Thermal analyses reveal that the compound melts at 449.7 K and is stable up to 560.0 K under a dynamic air atmosphere. Photoluminescence measurements show that the compound exhibits a blue fluorescence and a green phosphorescence associated with spin-allowed ( 1π← 1π*) and spin-forbidden ( 1π← 3π*) transitions, respectively. As a result, the average luminescence lifetime was determined to be 1.40 ns for the short-lived ( 1π← 1π*) transition and 105 ms for the long-lived ( 1π← 3π*) transition.
Authors:
ORCiD logo [1] ; ORCiD logo [2] ;  [3]
  1. Ames Lab., Ames, IA (United States)
  2. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States); Stockholm Univ., Stockholm (Sweden); Wroclaw Research Centre EIT+, Wroclaw (Poland)
  3. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States); Stockholm Univ., Stockholm (Sweden)
Publication Date:
Report Number(s):
IS-J-9692
Journal ID: ISSN 2053-2296; ACSCGG; PII: S2053229618005272
Grant/Contract Number:
AC02-07CH11358
Type:
Accepted Manuscript
Journal Name:
Acta Crystallographica. Section C, Structural Chemistry (Online)
Additional Journal Information:
Journal Name: Acta Crystallographica. Section C, Structural Chemistry (Online); Journal Volume: 74; Journal Issue: 6; Journal ID: ISSN 2053-2296
Publisher:
International Union of Crystallography
Research Org:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; carboxyl-functionalized imidazolium salt; hydrogen-bonding inter­action; thermal analysis; photoluminescence spectroscopy; crystal structure; ionic liquids
OSTI Identifier:
1455215

Prodius, Denis, Wilk-Kozubek, Magdalena, and Mudring, Anja -Verena. Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride. United States: N. p., Web. doi:10.1107/S2053229618005272.
Prodius, Denis, Wilk-Kozubek, Magdalena, & Mudring, Anja -Verena. Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride. United States. doi:10.1107/S2053229618005272.
Prodius, Denis, Wilk-Kozubek, Magdalena, and Mudring, Anja -Verena. 2018. "Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride". United States. doi:10.1107/S2053229618005272.
@article{osti_1455215,
title = {Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride},
author = {Prodius, Denis and Wilk-Kozubek, Magdalena and Mudring, Anja -Verena},
abstractNote = {A microcrystalline carboxyl-functionalized imidazolium chloride, namely 1-carboxymethyl-3-ethylimidazolium chloride, C7H11N2O2+·Cl–, has been synthesized and characterized by elemental analysis, attenuated total reflectance Fourier transform IR spectroscopy (ATR-FT-IR), single-crystal X-ray diffraction, thermal analysis (TGA/DSC), and photoluminescence spectroscopy. In the crystal structure, cations and anions are linked by C—H...Cl and C—H...O hydrogen bonds to create a helix along the [010] direction. Adjacent helical chains are further interconnected through O—H...Cl and C—H...O hydrogen bonds to form a (101¯) layer. Finally, neighboring layers are joined together via C—H...Cl contacts to generate a three-dimensional supramolecular architecture. Thermal analyses reveal that the compound melts at 449.7 K and is stable up to 560.0 K under a dynamic air atmosphere. Photoluminescence measurements show that the compound exhibits a blue fluorescence and a green phosphorescence associated with spin-allowed (1π←1π*) and spin-forbidden (1π←3π*) transitions, respectively. As a result, the average luminescence lifetime was determined to be 1.40 ns for the short-lived (1π←1π*) transition and 105 ms for the long-lived (1π←3π*) transition.},
doi = {10.1107/S2053229618005272},
journal = {Acta Crystallographica. Section C, Structural Chemistry (Online)},
number = 6,
volume = 74,
place = {United States},
year = {2018},
month = {5}
}

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