Gold (III)-2,2´-Bipyridine(bpy)-Arylazoimidazole (RaaiR’) Complexes: Synthesis and Spectral Charecterisation

Prithwiraj Byabartta

Abstract


Reaction of [Au(bpy)Cl2]PF6 with AgOTf followed by ligand addition leads to [Au(bpy)(RaaiR/)] in low yield whereas direct substitution gives high yield. [RaaiR/ = p-R-C6H4-N=N-C3H2-NN-1-R/, (1-3), abbreviated as N,N/-chelator, where N(imidazole) and N(azo) represent N and N/, respectively; R = H (a), Me (b), Cl (c) and R/ = Me (1), CH2CH3 (2), CH2Ph (3), OSO2CF3 is the triflate anion, bpy is 2,2´-bipyridine]. The 1H NMR spectral measurements suggest methylene, –CH2–, in RaaiEt gives a complex AB type multiplet while in RaaiCH2Ph it shows AB type quartets. 13C NMR spectrum reflect molecular skeleton. In the 1H-1H COSY spectrum of the present complexesand contour peaks in the 1H-13C HMQC spectrum in the present complexes, assign the solution structure.

Keywords


gold(III), arylazoimidazole, NMR, IR, ESIMS, bpy.

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Alejandro Gutiérrez, Javier Bernal, M. Dolores Villacampa, Carlos Cativiela, Antonio Laguna, and M. Concepción Gimeno, Synthesis of New Gold(I) Thiolates Containing Amino Acid Moieties with Potential Biological Interest, Inorg. Chem., 2013, 52 (11), pp 6473–6480Publication Date (Web): May 20, 2013 (Article)DOI: 10.1021/ic4003803

Yukatsu Shichibu and Katsuaki Konishi Electronic Properties of [Core+exo]-type Gold Clusters: Factors Affecting the Unique Optical Transitions Inorg. Chem., 2013, 52 (11), pp 6570–6575 Publication Date (Web): May 16, 2013 (Article) DOI: 10.1021/ic4005592

Zhongping Ou, Tony Khoury, Yuanyuan Fang, Weihua Zhu, Paul J. Sintic, Maxwell J. Crossley, and Karl M. Kadish Gold(III) Porphyrins Containing Two, Three, or Four β,β′-Fused Quinoxalines. Synthesis, Electrochemistry, and Effect of Structure and Acidity on Electroreduction Mechanism Inorg. Chem., 2013, 52 (5), pp 2474–2483 Publication Date (Web): February 20, 2013 (Article) DOI: 10.1021/ic302380z

Sang Ho Lim, Jennifer C. Schmitt, Jason Shearer, Jianhua Jia, Marilyn M. Olmstead, James C. Fettinger, and Alan L. Balch Crystallographic and Computational Studies of Luminescent, Binuclear Gold(I) Complexes, AuI2(Ph2P(CH2)nPPh2)2I2 (n = 3–6) Inorg. Chem., 2013, 52 (2), pp 823–831Publication Date (Web): January 9, 2013 (Article)DOI: 10.1021/ic301954n

Mehmet Ali Celik, Chandrakanta Dash, Venkata A. K. Adiraju, Animesh Das, Muhammed Yousufuddin, Gernot Frenking, and H. V. Rasika Dias End-On and Side-On π-Acid Ligand Adducts of Gold(I): Carbonyl, Cyanide, Isocyanide, and Cyclooctyne Gold(I) Complexes Supported by N-Heterocyclic Carbenes and PhosphinesInorg. Chem., 2013, 52 (2), pp 729–742Publication Date (Web): December 28, 2012 (Article)DOI: 10.1021/ic301869v

Athanassios C. Tsipis and Alexandros V. Stalikas Face-to-Face Stacks of Trinuclear Gold(I) Trihalides with Benzene, Hexafluorobenzene, and Borazine: Impact of Aromaticity on Stacking Interactions Inorg. Chem., 2013, 52 (2), pp 1047–1060 Publication Date (Web): December 27, 2012 (Article)DOI: 10.1021/ic302353t

Camille Latouche, Yu-Chen Lee, Jian-Hong Liao, Eric Furet, Jean-Yves Saillard, C. W. Liu, and Abdou Boucekkine Structure and Spectroscopic Properties of Gold(I) Diselenophosph(in)ate Complexes: A Joint Experimental and Theoretical Study Inorg. Chem., 2012, 51 (21), pp 11851–11859 Publication Date (Web): October 25, 2012 (Article)DOI: 10.1021/ic301763k

Víctor Rojas-Cervellera, Ernest Giralt, and Carme Rovira

Staple Motifs, Initial Steps in the Formation of Thiolate-Protected Gold Nanoparticles: How Do They Form?Inorg. Chem., 2012, 51 (21), pp 11422–11429Publication Date (Web): October 10, 2012 (Article)DOI: 10.1021/ic301079k

Dmitriy S. Dolzhnikov, Maria C. Iapalucci, Giuliano Longoni, Cristina Tiozzo, Stefano Zacchini, and Cristina Femoni New High-Nuclearity Carbonyl and Carbonyl-Substituted Rhodium Clusters and Their Relationships with Polyicosahedral Carbonyl-Substituted Palladium- and Gold-ThiolatesInorg. Chem., 2012, 51 (21), pp 11214–11216Publication Date (Web): October 8, 2012 (Communication)DOI: 10.1021/ic3011508

Mao-Sheng Miao, Joshua A. Kurzman, Nisha Mammen, Shobhana Narasimhan, and Ram Seshadri Trends in the Electronic Structure of Extended Gold Compounds: Implications for Use of Gold in Heterogeneous CatalysisInorg. Chem., 2012, 51 (14), pp 7569–7578

Publication Date (Web): July 5, 2012 (Article)DOI: 10.1021/ic3002674

Lei Gao, Nihal Deligonul, and Thomas G. Gray Gold(I) Complexes of Brominated Azadipyrromethene LigandsInorg. Chem., 2012, 51 (14), pp 7682–7688Publication Date (Web): July 3, 2012 (Article)DOI: 10.1021/ic300709n

Laura Rodríguez, Montserrat Ferrer, Ramon Crehuet, Josep Anglada, and João Carlos Lima Correlation between Photophysical Parameters and Gold–Gold Distances in Gold(I) (4-Pyridyl)ethynyl ComplexesInorg. Chem., 2012, 51 (14), pp 7636–7641Publication Date (Web): June 28, 2012 (Article)DOI: 10.1021/ic300609f

Volodymyr Smetana, Gordon J. Miller, and John D. Corbett Three Alkali-Metal–Gold–Gallium Systems. Ternary Tunnel Structures and Some Problems with Poorly Ordered CationsInorg. Chem., 2012, 51 (14), pp 7711–7721Publication Date (Web): June 27, 2012 (Article)DOI: 10.1021/ic300740u

Igor O. Koshevoy, Yuh-Chia Chang, Antti J. Karttunen, Stanislav I. Selivanov, Janne Jänis, Matti Haukka, Tapani Pakkanen, Sergey P. Tunik, and Pi-Tai Chou Intensely Luminescent Homoleptic Alkynyl Decanuclear Gold(I) Clusters and Their Cationic Octanuclear Phosphine DerivativesInorg. Chem., 2012, 51 (13), pp 7392–7403Publication Date (Web): June 11, 2012 (Article)DOI: 10.1021/ic300856h

Madanakrishna Katari, Mitta Nageswar Rao, Gopalan Rajaraman, and Prasenjit Ghosh Computational Insight into a Gold(I) N-Heterocyclic Carbene Mediated Alkyne Hydroamination ReactionInorg. Chem., 2012, 51 (10), pp 5593–5604Publication Date (Web): May 7, 2012 (Article)DOI: 10.1021/ic2024605

Atiya T. Overton and Ahmed A. Mohamed Gold(III) Diazonium Complexes for Electrochemical Reductive GraftingInorg. Chem., 2012, 51 (10), pp 5500–5502Publication Date (Web): April 26, 2012 (Communication)DOI: 10.1021/ic300307z

Yifeng Wang, Offer Zeiri, Shelly Sharet, and Ira A. Weinstock Role of the Alkali-Metal Cation Size in the Self-Assembly of Polyoxometalate-Monolayer Shells on Gold NanoparticlesInorg. Chem., 2012, 51 (14), pp 7436–7438Publication Date (Web): April 19, 2012 (Communication)DOI: 10.1021/ic300431a

Yu-Peng Zhou, Mei Zhang, Yu-Hao Li, Qi-Rui Guan, Fang Wang, Zhuo-Jia Lin, Chi-Keung Lam, Xiao-Long Feng, and Hsiu-Yi Chao Mononuclear Gold(I) Acetylide Complexes with Urea Group: Synthesis, Characterization, Photophysics, and Anion Sensing PropertiesInorg. Chem., 2012, 51 (9), pp 5099–5109Publication Date (Web): April 9, 2012 (Article)

DOI: 10.1021/ic202608r

Gemma E. Craig, Sarah D. Brown, Dimitrios A. Lamprou, Duncan Graham, and Nial J. Wheate Cisplatin-Tethered Gold Nanoparticles That Exhibit Enhanced Reproducibility, Drug Loading, and Stability: a Step Closer to Pharmaceutical Approval?Inorg. Chem., 2012, 51 (6), pp 3490–3497Publication Date (Web): March 5, 2012 (Article)DOI: 10.1021/ic202197g

Javier A. Cabeza, José M. Fernández-Colinas, Pablo García-Álvarez, and Diego Polo Diaminogermylene and Diaminostannylene Derivatives of Gold(I): Novel AuM and AuM2 (M = Ge, Sn) ComplexesInorg. Chem., 2012, 51 (6), pp 3896–3903Publication Date (Web): February 29, 2012 (Article)DOI: 10.1021/ic3001575

Ping Chai and John D. Corbett Gold Derivatives of Eight Rare-Earth-Metal-Rich Tellurides: Monoclinic R7Au2Te2 and Orthorhombic R6AuTe2 TypesInorg. Chem., 2012, 51 (6), pp 3548–3556Publication Date (Web): February 24, 2012 (Article)DOI: 10.1021/ic202342v

Maria Serratrice, Maria A. Cinellu, Laura Maiore, Maria Pilo, Antonio Zucca, Chiara Gabbiani, Annalisa Guerri, Ida Landini, Stefania Nobili, Enrico Mini, and Luigi Messori Synthesis, Structural Characterization, Solution Behavior, and in Vitro Antiproliferative Properties of a Series of Gold Complexes with 2-(2′-Pyridyl)benzimidazole as Ligand: Comparisons of Gold(III) versus Gold(I) and Mononuclear versus Binuclear Derivatives

Inorg. Chem., 2012, 51 (5), pp 3161–3171Publication Date (Web): February 17, 2012 (Article)DOI: 10.1021/ic202639t

Hanan E. Abdou, Ahmed A. Mohamed, José M. López-de-Luzuriaga, Miguel Monge, and John P. Fackler, Jr. Fine-Tuning the Luminescence and HOMO–LUMO Energy Levels in Tetranuclear Gold(I) Fluorinated Amidinate Complexes

Inorg. Chem., 2012, 51 (4), pp 2010–2015Publication Date (Web): January 30, 2012 (Article)

DOI: 10.1021/ic2010634

Marco Baron, Cristina Tubaro, Andrea Biffis, Marino Basato, Claudia Graiff, Albert Poater, Luigi Cavallo, Nicola Armaroli, and Gianluca Accorsi Blue-Emitting Dinuclear N-heterocyclic Dicarbene Gold(I) Complex Featuring a Nearly Unit Quantum YieldInorg. Chem., 2012, 51 (3), pp 1778–1784Publication Date (Web): January 23, 2012 (Article)

DOI: 10.1021/ic2020786

Bin Li, Yu-Hui Wu, Hui-Min Wen, Lin-Xi Shi, and Zhong-Ning Chen Gold(I)-Coordination Triggered Multistep and Multiple Photochromic Reactions in Multi-Dithienylethene (DTE) SystemsInorg. Chem., 2012, 51 (3), pp 1933–1942Publication Date (Web): January 18, 2012 (Article)DOI: 10.1021/ic202265u

Pedro I. da S. Maia, Hung Huy Nguyen, Daniela Ponader, Adelheid Hagenbach, Silke Bergemann, Ronald Gust, Victor M. Deflon, and Ulrich Abram Neutral Gold Complexes with Tridentate SNS Thiosemicarbazide LigandsInorg. Chem., 2012, 51 (3), pp 1604–1613

Publication Date (Web): January 10, 2012 (Article)DOI: 10.1021/ic201905t

Naween Dahal and Viktor Chikan Synthesis of Hafnium Oxide-Gold Core–Shell NanoparticlesInorg. Chem., 2012, 51 (1), pp 518–522Publication Date (Web): December 16, 2011 (Article)DOI: 10.1021/ic201977d

Tina H. T. Hsu, Jaishri J. Naidu, Bi-Jiuan Yang, Meng-Ying Jang, and Ivan J. B. Lin Self-Assembly of Silver(I) and Gold(I) N-Heterocyclic Carbene Complexes in Solid State, Mesophase, and SolutionInorg. Chem., 2012, 51 (1), pp 98–108

Publication Date (Web): December 2, 2011 (Article)DOI: 10.1021/ic2011343

Kolle E. Thomas, Abraham B. Alemayehu, Jeanet Conradie, Christine Beavers, and Abhik Ghosh Synthesis and Molecular Structure of Gold TriarylcorrolesInorg. Chem., 2011, 50 (24), pp 12844–12851Publication Date (Web): November 23, 2011 (Article)

DOI: 10.1021/ic202023r

Zhongping Ou, Weihua Zhu, Yuanyuan Fang, Paul J. Sintic, Tony Khoury, Maxwell J. Crossley, and Karl M. Kadish Unusual Multi-Step Sequential AuIII/AuII Processes of Gold(III) Quinoxalinoporphyrins in Acidic Non-Aqueous MediaInorg. Chem., 2011, 50 (24), pp 12802–12809Publication Date (Web): November 9, 2011 (Article)DOI: 10.1021/ic2019567

Yuan Yuan, Ning Yan, and Paul J. Dyson pH-Sensitive Gold Nanoparticle Catalysts for the Aerobic Oxidation of AlcoholsInorg. Chem., 2011, 50 (21), pp 11069–11074Publication Date (Web): October 10, 2011 (Article)

DOI: 10.1021/ic201608j

Jeffrey W. Hudgens, John M. Pettibone, Thomas P. Senftle, and Ryan N. Bratton Reaction Mechanism Governing Formation of 1,3-Bis(diphenylphosphino)propane-Protected Gold NanoclustersInorg. Chem., 2011, 50 (20), pp 10178–10189Publication Date (Web): September 19, 2011 (Article)DOI: 10.1021/ic2018506

Margot Wenzel, Benoît Bertrand, Marie-Joëlle Eymin, Virginie Comte, Jennifer A. Harvey, Philippe Richard, Michael Groessl, Olivier Zava, Hedi Amrouche, Pierre D. Harvey, Pierre Le Gendre, Michel Picquet, and Angela Casini Multinuclear Cytotoxic Metallodrugs: Physicochemical Characterization and Biological Properties of Novel Heteronuclear Gold–Titanium ComplexesInorg. Chem., 2011, 50 (19), pp 9472–9480Publication Date (Web): August 29, 2011 (Article)DOI: 10.1021/ic201155y

Olga Crespo, M. Concepción Gimeno, Antonio Laguna, Fernando J. Lahoz, and Carmen Larraz Unprecedented Luminescent Heteropolynuclear Aggregates with Gold Thiolates as Building BlocksInorg. Chem., 2011, 50 (19), pp 9533–9544Publication Date (Web): August 23, 2011 (Article)DOI: 10.1021/ic201245q

Elisabete Oliveira, Cristina Nuñez, Benito Rodríguez-González, José Luis Capelo, and Carlos Lodeiro Novel Small Stable Gold Nanoparticles Bearing Fluorescent Cysteine–Coumarin Probes as New Metal-Modulated ChemosensorsInorg. Chem., 2011, 50 (18), pp 8797–8807

Publication Date (Web): August 17, 2011 (Article)DOI: 10.1021/ic200664z

Elisabete Oliveira, Damiano Genovese, Riccardo Juris, Nelsi Zaccheroni, José Luis Capelo, M. Manuela M. Raposo, Susana P. G. Costa, Luca Prodi, and Carlos Lodeiro Bioinspired Systems for Metal-Ion Sensing: New Emissive Peptide Probes Based on Benzo[d]oxazole Derivatives and Their Gold and Silica NanoparticlesInorg. Chem., 2011, 50 (18), pp 8834–8849Publication Date (Web): August 17, 2011 (Article)DOI: 10.1021/ic200792t

Rubén Chico, Eva Castillejos, Philippe Serp, Silverio Coco, and Pablo Espinet Alkynylisocyanide Gold Mesogens as Precursors of Gold NanoparticlesInorg. Chem., 2011, 50 (17), pp 8654–8662Publication Date (Web): August 4, 2011 (Article)DOI: 10.1021/ic201210p

Hsin-Lun Wu, Huei-Ru Tsai, Yun-Ting Hung, Ka-Un Lao, Ching-Wen Liao, Pei-Ju Chung, Jer-Shing Huang, I-Chia Chen, and Michael H. Huang A Comparative Study of Gold Nanocubes, Octahedra, and Rhombic Dodecahedra as Highly Sensitive SERS Substrates

Inorg. Chem., 2011, 50 (17), pp 8106–8111Publication Date (Web): July 28, 2011 (Article)

DOI: 10.1021/ic200504n

Ilaria Biondi, Gábor Laurenczy, and Paul J. Dyson Synthesis of Gold Nanoparticle Catalysts Based on a New Water-Soluble Ionic PolymerInorg. Chem., 2011, 50 (17), pp 8038–8045Publication Date (Web): July 27, 2011 (Article)DOI: 10.1021/ic200334m

Corinna Wetzel, Peter C. Kunz, Indre Thiel, and Bernhard Spingler Gold(I) Catalysts with Bifunctional P, N LigandsInorg. Chem., 2011, 50 (16), pp 7863–7870Publication Date (Web): July 15, 2011 (Article)DOI: 10.1021/ic2011259

Saroj L. Samal and John D. Corbett Relativistic Effects and Gold Site Distributions: Synthesis, Structure, and Bonding in a Polar Intermetallic Na6Cd16Au7

Inorg. Chem., 2011, 50 (15), pp 7033–7039Publication Date (Web): July 5, 2011 (Article)

DOI: 10.1021/ic200501

José M. López-de-Luzuriaga, Miguel Monge, M. Elena Olmos, David Pascual, and María Rodríguez-Castillo Influence of the Electronic Characteristics of N-Donor Ligands in the Excited State of Heteronuclear Gold(I)–Copper(I) SystemsInorg. Chem., 2011, 50 (15), pp 6910–6921Publication Date (Web): June 30, 2011 (Article)DOI: 10.1021/ic102550z

Jai Anand Garg, Olivier Blacque, and Koushik Venkatesan Syntheses and Photophysical Properties of Luminescent Mono-cyclometalated Gold(III) cis-Dialkynyl Complexes

Inorg. Chem., 2011, 50 (12), pp 5430–5441Publication Date (Web): May 23, 2011 (Article)

DOI: 10.1021/ic102216v

Roberto Cao, Jr., Reynaldo Villalonga, Alicia M. Díaz-García, Roberto Cao, Teofilo Rojo, and M. Carmen Rodríguez-Argüelles Gold Nanoparticles Enhancing Dismutation of Superoxide Radical by Its Bis(dithiocarbamato)copper(II) ShellInorg. Chem., 2011, 50 (11), pp 4705–4712Publication Date (Web): April 26, 2011 (Article)DOI: 10.1021/ic101770h

H. V. Rasika Dias, Chandrakanta Dash, Muhammed Yousufuddin, Mehmet Ali Celik, and Gernot Frenking Cationic Gold Carbonyl Complex on a Phosphine Support

Inorg. Chem., 2011, 50 (10), pp 4253–4255Publication Date (Web): April 20, 2011 (Communication)DOI: 10.1021/ic200757j

Doris Y. Melgarejo, Gina M. Chiarella, John P. Fackler, Jr., Lisa M. Perez, Alexandre Rodrigue-Witchel, and Christian Reber Synthesis and Structure of a Dinuclear Gold(II) Complex with Terminal Fluoride LigandsInorg. Chem., 2011, 50 (10), pp 4238–4240

Publication Date (Web): April 14, 2011 (Communication)DOI: 10.1021/ic200394q

Adriana Ilie, Ciprian I. Raţ, Susanne Scheutzow, Christiane Kiske, Karin Lux, Thomas M. Klapötke, Cristian Silvestru, and Konstantin Karaghiosoff Metallophilic Bonding and Agostic Interactions in Gold(I) and Silver(I) Complexes Bearing a Thiotetrazole Unit

Inorg. Chem., 2011, 50 (6), pp 2675–2684Publication Date (Web): February 10, 2011 (Article)DOI: 10.1021/ic102595d

Qisheng Lin and John D. Corbett Ca14Au46Sn5: a “Colored” Gd14Ag51-Type Structure Containing Columns of Well-Differentiated Hexagonal Gold StarsInorg. Chem., 2011, 50 (5), pp 1808–1815Publication Date (Web): January 21, 2011 (Article)DOI: 10.1021/ic102243c

Manoja K. Samantaray, Chandrakanta Dash, Mobin M. Shaikh, Keliang Pang, Ray J. Butcher, and Prasenjit Ghosh Gold(III) N-Heterocyclic Carbene Complexes Mediated Synthesis of β-Enaminones From 1,3-Dicarbonyl Compounds and Aliphatic Amines

Inorg. Chem., 2011, 50 (5), pp 1840–1848Publication Date (Web): January 21, 2011 (Article)

DOI: 10.1021/ic102268n

Carrie A. Simpson, Christopher L. Farrow, Peng Tian, Simon J. L. Billinge, Brian J. Huffman, Kellen M. Harkness, and David E. Cliffel Tiopronin Gold Nanoparticle Precursor Forms Aurophilic Ring TetramerInorg. Chem., 2010, 49 (23), pp 10858–10866Publication Date (Web): November 10, 2010 (Article)DOI: 10.1021/ic101146e

Angela M. Kuchison, Michael O. Wolf, and Brian O. PatrickPhotophysical Properties and Electropolymerization of Gold Complexes of 3,3′′-Diethynyl-2,2′:5′,2′′-terthiophene

Inorg. Chem., 2010, 49 (19), pp 8802–8812Publication Date (Web): September 1, 2010 (Article)DOI: 10.1021/ic100961w

Maria José Calhorda, Carmen Ceamanos, Olga Crespo, M. Concepción Gimeno, Antonio Laguna, Carmen Larraz, Pedro D. Vaz, and M. Dolores Villacampa Heteropolynuclear Gold Complexes with Metallophilic Interactions: Modulation of the Luminescent Properties

Inorg. Chem., 2010, 49 (18), pp 8255–8269Publication Date (Web): August 19, 2010 (Article)DOI: 10.1021/ic100413x

Hong-Jhin You, Ching-Shiang Fang, Ju-Ling Lin, Shih-Sheng Sun and C. W. Liu Dinuclear Gold Diselenophosphate Complexes: Structures and PhotoluminescenceInorg. Chem., 2010, 49 (17), pp 7641–7643Publication Date (Web): August 9, 2010 (Communication)

DOI: 10.1021/ic101390e

Camino Bartolomé, Domingo García-Cuadrado, Zoraida Ramiro, and Pablo EspinetSynthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of Vinyl Arenes and in Intramolecular Hydroalkoxylation of AllenesInorg. Chem., 2010, 49 (21), pp 9758–9764

Publication Date (Web): July 8, 2010 (Article)DOI: 10.1021/ic101059c

Sebastián A. Suárez, Mariano H. Fonticelli, Aldo A. Rubert, Ezequiel de la Llave, Damián Scherlis, Roberto C. Salvarezza, Marcelo A. Martí and Fabio Doctorovich

A Surface Effect Allows HNO/NO Discrimination by a Cobalt Porphyrin Bound to GoldInorg. Chem., 2010, 49 (15), pp 6955–6966Publication Date (Web): July 6, 2010 (Article)DOI: 10.1021/ic1007022

Masashi Saitoh, Alan L. Balch, Junpei Yuasa and Tsuyoshi Kawai Effects of Counter Anions on Intense Photoluminescence of 1-D Chain Gold(I) ComplexesInorg. Chem., 2010, 49 (15), pp 7129–7134Publication Date (Web): June 28, 2010 (Article)DOI: 10.1021/ic100948m


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