ICCAS OpenIR
Syntheses, Structures, and Fluorescent Properties of 2-(1H-Imidazol-2-yl)phenols and Their Neutral Zn(II) Complexes
Eseola, Abiodun Omokehinde3,4; Li, Wen4; Gao, Rong1,2; Zhang, Min1,2; Hao, Xiang1,2; Liang, Tongling1,2; Obi-Egbedi, Nelson Okpako3; Sun, Wen-Hua1,2
2009-10-05
Source PublicationINORGANIC CHEMISTRY
ISSN0020-1669
Volume48Issue:19Pages:9133-9146
AbstractA series of 2-(imidazole-2-yl)phenol ligands L1-L6 with the general composition 4-R(4)-5-R(3)-6-R(2)-2-(4,5-R(1),R(1)-1H-imidazole-2-yl)phenol (L1: R(1) = C(2)H(5), R(2) = R(3) = R(4) = H; L2: R(1) = C(6)H(5), R(2) = R(3) = R(4) = H; L3: R(1) = C(6)H(5), R(3) = OCH(3), R(2) = R(4) = H; L4: R(1) = C(6)H(5), R(4) = OCH(3), R(2) = R(3) = H; L5: R(1) = C(6)H(5), R(3) = H, R(2) = R(4) = CH(3); L(6): R(1) = C(6)H(5), R(3) = H, R(2) = R(4) = t-Bu) and L7 (2,4-di-tert-butyl-6-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol) and their neutral Zn(II) complexes (Z1-Z7) were synthesized and characterized by spectroscopic and elemental analyses. Molecular structures of L1, L5, Z1, and Z2 were confirmed by single-crystal X-ray diffraction. L1 crystallized in the monoclinic Cc space group, while L5, Z1, and Z2 all crystallized in the triclinic P (1) over bar space group. One-dimensional arrays based on continuous pi-pi stacking interactions and hydrogen bonding were observed for L1 and Z1, while L5 existed as discrete dimeric stack units. Z2 formed hydrogen-bonded 1D network structures but was completely devoid of pi-pi stacking interactions. Emission processes were found to be more dependent on the substituents on phenol as well as condensed media. In contrast to general conclusions on closely related systems in the literature, significant photorelaxation from the excited enol state was observed in the cases of L1 in methanol and L4 in both THF and methanol. Therefore, there exists a certain unusual hindering factor to keto-enol phototautomerism in the ligand-solvent systems. The sensing property of zinc(II) complexes was explored regarding the effects of substituents in their ligands. It was observed that coordination to the zinc(II) ion led to emission quenching for L1 and L2 while causing an enhancement of fluorescent intensity for L3, L4, L5, and L6. A linear relationship was observed between the emission intensity and the concentration of the zinc ion at the 10(-8) M level. Compared to other zinc compounds in this work, fluorescence enhancement in Z3 and Z4 showed that the methoxyl substituent is favorable for fluorescent enhancement.
DOI10.1021/ic9008703
Indexed BySCI
Language英语
WOS IDWOS:000270091000018
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:49[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67152
Collection中国科学院化学研究所
Corresponding AuthorSun, Wen-Hua
Affiliation1.Chinese Acad Sci, Key Lab Engn Plast, Inst Chem, Beijing 100190, Peoples R China
2.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
3.Redeemers Univ, Dept Chem Sci, Redemption City, Ogun, Nigeria
4.Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Eseola, Abiodun Omokehinde,Li, Wen,Gao, Rong,et al. Syntheses, Structures, and Fluorescent Properties of 2-(1H-Imidazol-2-yl)phenols and Their Neutral Zn(II) Complexes[J]. INORGANIC CHEMISTRY,2009,48(19):9133-9146.
APA Eseola, Abiodun Omokehinde.,Li, Wen.,Gao, Rong.,Zhang, Min.,Hao, Xiang.,...&Sun, Wen-Hua.(2009).Syntheses, Structures, and Fluorescent Properties of 2-(1H-Imidazol-2-yl)phenols and Their Neutral Zn(II) Complexes.INORGANIC CHEMISTRY,48(19),9133-9146.
MLA Eseola, Abiodun Omokehinde,et al."Syntheses, Structures, and Fluorescent Properties of 2-(1H-Imidazol-2-yl)phenols and Their Neutral Zn(II) Complexes".INORGANIC CHEMISTRY 48.19(2009):9133-9146.
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