Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units

Caihong Zhang; Lifeng Li; Hongjuan Wu; Zhixun Liu; Junfen Li; Guomei Zhang; Guangming Wen; Shaomin Shuang; Chuan Dong; Martin M.F. Choi

doi:10.1016/j.saa.2012.10.005

Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units

Caihong Zhang, Lifeng Li, Hongjuan Wu, Zhixun Liu, Junfen Li, Guomei Zhang, Guangming Wen, Shaomin Shuang, Chuan Dong^*, Martin M.F. Choi

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

6 Citations (Scopus)

Abstract

A series of oxazole derivatives, 5-methyl-2-(p-methylphenyl)-4-acetyl oxazole (MMPAO), 5-methyl-2-(p-methoxyphenyl)-4-acetyl oxazole (MOPAO), 5-methyl-2-(p-N,N′-dimethylamino-phenyl)-4-acetyl oxazole (MDMAPAO) and 5-methyl-2-(p-N,N′-diphenylaminophenyl)-4-acetyl oxazole (MDPAPAO) have been synthesized and studied to compare their photophysical properties. The UV-visible absorption spectra of MDMAPAO and MDPAPAO are bathochromatically shifted as compared to that of MMPAO and MOPAO. The fluorescence emission of MDPAPAO is very sensitive to the polarity of solvents. The magnitude of change in the dipole moment was calculated using the Lippert-Mataga equation. MDPAPAO shows the highest change in the dipole moment (Δu = 13.3D) than that of the other three oxazole derivatives. The spectral properties including fluorescence quantum yield and lifetime were determined in solvents with different polarities. MDPAPAO displays the highest fluorescence quantum yield and lifetime, following a bi-exponential fluorescent decay fashion. Our result demonstrates that the excited state of MDPAPAO possesses the property of intramolecular charge transfer.

Original language	English
Pages (from-to)	256-262
Number of pages	7
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	102
DOIs	https://doi.org/10.1016/j.saa.2012.10.005
Publication status	Published - Feb 2013

Scopus Subject Areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

User-Defined Keywords

Charge transfer
Fluorescence
Interaction
Oxazole ring

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10.1016/j.saa.2012.10.005

Cite this

@article{f6a962418977452f869cd0679e641dc9,

title = "Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units",

abstract = "A series of oxazole derivatives, 5-methyl-2-(p-methylphenyl)-4-acetyl oxazole (MMPAO), 5-methyl-2-(p-methoxyphenyl)-4-acetyl oxazole (MOPAO), 5-methyl-2-(p-N,N′-dimethylamino-phenyl)-4-acetyl oxazole (MDMAPAO) and 5-methyl-2-(p-N,N′-diphenylaminophenyl)-4-acetyl oxazole (MDPAPAO) have been synthesized and studied to compare their photophysical properties. The UV-visible absorption spectra of MDMAPAO and MDPAPAO are bathochromatically shifted as compared to that of MMPAO and MOPAO. The fluorescence emission of MDPAPAO is very sensitive to the polarity of solvents. The magnitude of change in the dipole moment was calculated using the Lippert-Mataga equation. MDPAPAO shows the highest change in the dipole moment (Δu = 13.3D) than that of the other three oxazole derivatives. The spectral properties including fluorescence quantum yield and lifetime were determined in solvents with different polarities. MDPAPAO displays the highest fluorescence quantum yield and lifetime, following a bi-exponential fluorescent decay fashion. Our result demonstrates that the excited state of MDPAPAO possesses the property of intramolecular charge transfer.",

keywords = "Charge transfer, Fluorescence, Interaction, Oxazole ring",

author = "Caihong Zhang and Lifeng Li and Hongjuan Wu and Zhixun Liu and Junfen Li and Guomei Zhang and Guangming Wen and Shaomin Shuang and Chuan Dong and Choi, {Martin M.F.}",

note = "Funding Information: The work described in this paper was supported by the National Nature Science Foundation (Nos. 21175086 and 21105060 ) and the Science Foundation of Shanxi Province ( 2012011007-2 ).",

year = "2013",

month = feb,

doi = "10.1016/j.saa.2012.10.005",

language = "English",

volume = "102",

pages = "256--262",

journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",

issn = "1386-1425",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units

AU - Zhang, Caihong

AU - Li, Lifeng

AU - Wu, Hongjuan

AU - Liu, Zhixun

AU - Li, Junfen

AU - Zhang, Guomei

AU - Wen, Guangming

AU - Shuang, Shaomin

AU - Dong, Chuan

AU - Choi, Martin M.F.

N1 - Funding Information: The work described in this paper was supported by the National Nature Science Foundation (Nos. 21175086 and 21105060 ) and the Science Foundation of Shanxi Province ( 2012011007-2 ).

PY - 2013/2

Y1 - 2013/2

N2 - A series of oxazole derivatives, 5-methyl-2-(p-methylphenyl)-4-acetyl oxazole (MMPAO), 5-methyl-2-(p-methoxyphenyl)-4-acetyl oxazole (MOPAO), 5-methyl-2-(p-N,N′-dimethylamino-phenyl)-4-acetyl oxazole (MDMAPAO) and 5-methyl-2-(p-N,N′-diphenylaminophenyl)-4-acetyl oxazole (MDPAPAO) have been synthesized and studied to compare their photophysical properties. The UV-visible absorption spectra of MDMAPAO and MDPAPAO are bathochromatically shifted as compared to that of MMPAO and MOPAO. The fluorescence emission of MDPAPAO is very sensitive to the polarity of solvents. The magnitude of change in the dipole moment was calculated using the Lippert-Mataga equation. MDPAPAO shows the highest change in the dipole moment (Δu = 13.3D) than that of the other three oxazole derivatives. The spectral properties including fluorescence quantum yield and lifetime were determined in solvents with different polarities. MDPAPAO displays the highest fluorescence quantum yield and lifetime, following a bi-exponential fluorescent decay fashion. Our result demonstrates that the excited state of MDPAPAO possesses the property of intramolecular charge transfer.

AB - A series of oxazole derivatives, 5-methyl-2-(p-methylphenyl)-4-acetyl oxazole (MMPAO), 5-methyl-2-(p-methoxyphenyl)-4-acetyl oxazole (MOPAO), 5-methyl-2-(p-N,N′-dimethylamino-phenyl)-4-acetyl oxazole (MDMAPAO) and 5-methyl-2-(p-N,N′-diphenylaminophenyl)-4-acetyl oxazole (MDPAPAO) have been synthesized and studied to compare their photophysical properties. The UV-visible absorption spectra of MDMAPAO and MDPAPAO are bathochromatically shifted as compared to that of MMPAO and MOPAO. The fluorescence emission of MDPAPAO is very sensitive to the polarity of solvents. The magnitude of change in the dipole moment was calculated using the Lippert-Mataga equation. MDPAPAO shows the highest change in the dipole moment (Δu = 13.3D) than that of the other three oxazole derivatives. The spectral properties including fluorescence quantum yield and lifetime were determined in solvents with different polarities. MDPAPAO displays the highest fluorescence quantum yield and lifetime, following a bi-exponential fluorescent decay fashion. Our result demonstrates that the excited state of MDPAPAO possesses the property of intramolecular charge transfer.

KW - Charge transfer

KW - Fluorescence

KW - Interaction

KW - Oxazole ring

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U2 - 10.1016/j.saa.2012.10.005

DO - 10.1016/j.saa.2012.10.005

M3 - Journal article

C2 - 23220665

AN - SCOPUS:84870323298

SN - 1386-1425

VL - 102

SP - 256

EP - 262

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

ER -

Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units

Abstract

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