- A rhenium complex doped in a silica molecular sieve for molecular oxygen sensing: Construction and characterization
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This paper reported a diamine ligand and its Re(I) complex for potential application in oxygen sensing. The novelty of this diamine ligand localized at its increased conjugation chain which had a typical electron-withdrawing group of 1,3,4-oxadiazole. Ele
- Yang, Xiaozhou,Li, Yanxiao
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Read Online
- Luminescent PhotoCORMs: Enabling/Disabling CO Delivery upon Blue Light Irradiation
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The new luminescent carbonyl compounds [Mn(Oxa-H)(CO)3Br] (1) and [Mn(Oxa-NMe2)(CO)3Br] (2) were synthesized and fully characterized. Complexes 1 and 2 showed CO release under blue light (λ453). Spectroscopic techniques and TD-DFT and SOC-TD-DFT calculati
- Amorim, André L.,Bregalda, Mayana B.,Camargo, Tiago P.,De Souza, Bernardo,Farias, Giliandro,Haukka, Matti,Nordlander, Ebbe,Peralta, Rosely A.,Weiss, Vitor C.,Xavier, Fernando R.
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supporting information
p. 13078 - 13090
(2020/10/09)
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- UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow
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A range of 1,3,4-oxadiazoles have been synthesized using a UV-B activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.
- Green, Luke,Livingstone, Keith,Bertrand, Sophie,Peace, Simon,Jamieson, Craig
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supporting information
p. 14866 - 14870
(2020/11/11)
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- Preparation and acetylcholinesterase inhibitory activities of pyridine-based 1,3,4-oxadiazole derivatives
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Fourteen pyridine-based 1,3,4-oxadiazole derivatives were synthesized from pyridine-2-carboxaldehyde via iodine-mediated oxidative cyclisation with substituted hydrazide by using the impregnation method. Their structures were confirmed by melting point,
- Chen, Yafang,Huang, Ling,Yang, Wude,Yu, Xiang,Zhou, Xingji
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p. 1163 - 1171
(2020/09/18)
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- Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides
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An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.
- Shang, Zhi-Hao,Sun, Ji-Na,Guo, Jiang-Shan,Sun, Yuan-Yuan,Weng, Wei-Zhao,Zhang, Zhen-Xiao,Li, Zeng-Jing,Zhu, Yan-Ping
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supporting information
(2020/01/08)
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- Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds: Via sp3 C-H functionalization of azaarenes
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An efficient iodine-mediated one-pot synthetic protocol for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C-H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions and high yields, making this protocol an attractive strategy towards the synthesis of bioactive molecules and their key building blocks.
- Mani, Geeta Sai,Donthiboina, Kavitha,Shankaraiah, Nagula,Kamal, Ahmed
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p. 15999 - 16006
(2019/10/28)
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- A series of blue-green-yellow-red emitting Cu(I) complexes: Molecular structure and photophysical performance
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In this work, we designed a series of [Cu(N–N)(PPh3)2]BF4 complexes with different optical edge values and emission colors from blue to red, where N–N and PPh3 denoted a diamine ligand and triphenylphosphine, respectively. Six N–N ligands with various conjugation chains (short π chain, modest π chain and long π chain) were selected. A systematical comparison between these Cu(I) complexes was performed, so that the correlation between N–N structure and [Cu(N–N)(PPh3)2] photophysical performance was tentatively discussed. Their single crystal structure was found consistent with literature ones, forming a typical tetrahedral coordination geometry. Density functional theory calculation indicated that their onset electronic transition showed a mixed character of metal-to-ligand-charge-transfer and ligand-to-ligand-charge-transfer. Detailed analysis on photophysical parameters suggested that the absorption edge of [Cu(N–N)(PPh3)2]BF4 complex was controlled by conjugation length in diamine ligand. A wide absorption edge needed a short conjugation chain in diamine ligand. Similar tendency was found for their emission spectra. In addition, a long conjugation chain in diamine ligand widened emission spectra obviously. Emission dynamics showed slim correlation with diamine ligand conjugation length since the excited state was controlled mainly by dynamic procedure and steric factor of diamine ligands.
- Zhang, Liming,Zuo, Qinghui
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- With piezochromic characteristic ion iridium complex and its preparation method and application
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The invention relates to an ionic type iridium complex with piezochromic characteristic as well as a preparation method and application thereof and in particular relates to an ionic type iridium complex (III) based on 1,3,4-oxadiazole N^N auxiliary ligand, wherein a structural formula of the ionic type iridium complex is shown as a formula (I) or a formula (II) in the specification. Synthesis steps of the ionic type iridium complex are simple, synthesis conditions are mild, and luminescence of an organic luminophor in a solid state is changed by virtue of external factors of heat, light, electricity, pressure and the like, wherein the phenomenon that the luminescence of the solid organic luminophor is changed by adopting a pressure or mechanical grinding manner is called as a piezochromic phenomenon. A piezochromic material has unique emitting colour changing and reversing properties, so that the ionic type iridium complex has great potential in application of record, data storage, sensors and the like.
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Paragraph 0032; 0033; 0034
(2017/06/30)
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- With aggregation inducing phosphorescent emission characteristic of the cationic iridium complex and application
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The invention relates to cationic iridium (III) complexes with an aggregation induced phosphorescence emission characteristic, and an application thereof, and concretely relates to cationic iridium (III) complexes based on 1,3,4-oxadiazole derivatives as an N^N auxiliary ligand. The structural general formula of the cationic iridium (III) complexes is represented by formula (I) shown in the specification. Ar in the formula (I) represents carbazole or substituted carbazole. The above materials have the advantages of simple synthesis steps, mild synthesis conditions, very weak even no luminescence in a solution and enhanced luminescence being triplet state emission in an aggregation state. The materials are expected to become commercialized potential organic optoelectronic functional materials.
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Paragraph 0025; 0026; 0027
(2017/08/25)
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- Orange-red- and white-emitting diodes fabricated by vacuum evaporation deposition of sublimable cationic iridium complexes
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Two novel red-emitting cationic iridium complexes, [Ir(ppy)2(pop)][B(5fph)4] (1) and [Ir(ppy)2(pop)][BArF24] (2), have been developed, where ppy is 2-phenylpyridine, pop is 2-(5-phenyl-1-1,3,4-oxadiazol-2-yl)pyridine, [B(5fph)4]- is tetrakis(pentafluorophenyl)borate and [BArF24]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, respectively. Photophysical properties of 1 and 2 in both solution and neat film were fully investigated, along with their photochemical, thermal and electrochemical stability. Interestingly, by introducing bulky tetraphenylborate derivatives as negative counter-ions, the volatility of 1 and 2 has been extremely improved, enabling fabrication of organic light-emitting diodes (OLEDs) by vacuum evaporation deposition. By doping these two sublimable cationic emitters into a DIC-TRZ (2,4-diphenyl-6-bis(12-phenylindolo[2,3-a]carbazole-11-yl)-1,3,5-triazine) host, we succeeded in the preparation of orange-red-emitting devices with a peak wavelength of 596 nm. 1-Based OLEDs showed a current efficiency of 4.5 cd A-1 and maximum brightness of 19.4 × 103 cd m-2, whereas 2-based OLEDs furnished a higher efficiency of 5.1 cd A-1. Then, we attained a white emission by doping 1 or 2 into a TCTA (4,4′,4′′-tris(carbazol-9-yl)triphenylamine) host at low concentrations. The 1-based white device featured a high colour rendering index (CRI) of 86 and good Commission International de L'EClairage (CIE) coordinates of (0.33, 0.34), quite close to the equal-energy-white-point (i.e., CIEx,y = 0.33, 0.33), and the 2-based white device showed a rather higher CRI of 89. To the best of our knowledge, this is the first report of white OLEDs fabricated by vacuum evaporation deposition of sublimable cationic iridium complexes, indicating their great potential for use in full-colour flat-panel display and lighting applications.
- Ma, Dongxin,Duan, Lian,Qiu, Yong
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supporting information
p. 5051 - 5058
(2016/06/15)
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- Synthesis, characterization and striking photoluminescence variation of a series of copper(I) complexes containing oxadiazole ligand
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A series of novel photoluminescent copper(I) complexes with the formula [Cu(P-P)(L)]BF4, where P-P = triphenylphosphine (PPh3) (1, 2), bis[2-(diphenylphosphino)phenyl]-ether (POP) (3, 4), L = 2-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazol
- Shi, Lin-Fang,Li, Bin,Zhang, Li-Ming,Zuo, Qing-Hui,Yue, Shumei
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- I2-mediated oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides
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A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A series of symmetrical and asymmetrical 2,5-disubstituted (aryl, alkyl, and/or vinyl) 1,3,4-oxadiazoles can be conveniently generated in an efficient and scalable fashion.
- Yu, Wenquan,Huang, Gang,Zhang, Yueteng,Liu, Hongxu,Dong, Lihong,Yu, Xuejun,Li, Yujiang,Chang, Junbiao
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p. 10337 - 10343
(2013/11/06)
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- Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles
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A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.
- Guin, Srimanta,Ghosh, Tuhin,Rout, Saroj Kumar,Banerjee, Arghya,Patel, Bhisma K.
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supporting information; experimental part
p. 5976 - 5979
(2012/01/02)
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- Molecular logic gates and switches based on 1,3,4-oxadiazoles triggered by metal ions
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Organic molecular devices for information processing applications are highly useful building blocks for constructing molecular-level machines. The development of "intelligent" molecules capable of performing logic operations would enable molecular-level devices and machines to be created. We designed a series of 2,5-diaryl-1,3,4oxadiazoles bearing a 2-(para-substituted) phenyl and a 5-(o-pyridyl) group (substituent X = NMe2, OEt, Me, H, and Cl; 1a-e) that form a bidentate chelating environment for metal ions. These compounds showed fluorescence response profiles varying in both emission intensity and wavelength toward the tested metal ions Ni2+, Cu 2+, Zn2+, Cd2+, Hg2+, and Pb 2+ and the respons-es were dependent on the substituent X, with those of 1d being the most substantial. The 1,3,4-oxadiazole O or N atom and pyridine N atom were identified as metal-chelating sites. The fluorescence responses of 1d upon metal chelation were employed for developing truth tables for OR, NOR, INHIBIT, and EnNOR logic gates as well as "ON-OFF-ON" and "OFF-ONOFF" fluorescent switches in a single 1,3,4-oxadiazole molecular system.
- Li, Ai-Fang,Ruan, Yi-Bin,Jiang, Qian-Qian,He, Wen-Bin,Jiang, Yun-Bao
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experimental part
p. 5794 - 5802
(2010/08/19)
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- Mild and convenient one-pot synthesis of 1,3,4-oxadiazoles
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A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted- 1,3,4-oxadiazoles in good to very good yields.
- Stabile, Paolo,Lamonica, Alessandro,Ribecai, Arianna,Castoldi, Damiano,Guercio, Giuseppe,Curcuruto, Ornella
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supporting information; experimental part
p. 4801 - 4805
(2010/10/02)
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- Synthesis, characterization, crystal structures, and photophysical properties of a series of room-temperature phosphorescent copper(I) complexes with oxadiazole-derived diimine ligand
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In this paper, we report four phosphorescent Cu(I) complexes of [Cu(OP)(PPh3J2]BF4, [Cu(MeOP)(PPh 3)2]BF4, [Cu(OP)(POP)]BF4, and [Cu(Me-OP)(POP)]BF4 with oxadiazole-de
- Wei, Fuxiang,Fang,Huang
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experimental part
p. 2600 - 2605
(2011/02/17)
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- Tetrazoles: LIII. Microwave-activated acylation of 5-substituted tetrazoles
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The acylation of 5-aryl(hetaryl)tetrazoles with acetic and benzoic anhydrides under microwave irradiation gave the corresponding 2-substituted 5-methyl-and 5-phenyl-1,3,4-oxadiazoles in high yields. The use of microwave activation reduces the reaction temperature by 30-40°C and shortens the reaction time by a factor of 5 to 7.
- Efimova,Artamonova,Koldobskii
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experimental part
p. 1345 - 1347
(2009/09/06)
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- APO AI EXPRESSION ACCELERATING AGENT
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Pharmaceutical compositions for enhancing the expression of apoAI are provided.Pharmaceutical compositions for enhancing the expression of apoAI which comprises a compound of formula (I): in which Y1 is O, S or NR1; Y2, Y
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