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DOI: 10.1055/s-0035-1561504
Metallocenium Chemistry and Its Emerging Impact on Synthetic Macromolecular Chemistry
Publication History
Received: 29 September 2015
Accepted after revision: 06 November 2015
Publication Date:
17 February 2016 (online)
Abstract
Cationic metallocenes (or metalloceniums) are a class of sandwich-type compounds with cationic metal centers, which are usually iron, cobalt, or rhodium. These unique charged complexes have received wide attention owing to both rich electrochemistry and the positive charge associated with the transition metal. They are potential building blocks for fabricating functional polyelectrolytes and for possible biomedical applications. As the basis of all metallocenium-containing materials, the synthetic chemistry of metallocenium has been a recently emerging field. In this account, we give a brief summary of metallocenium chemistry. Furthermore, its emerging impact on functional macromolecules is also covered.
1 Introduction
2 Cobaltocenium-Containing Derivatives and Macromolecules
2.1 General Synthetic Routes
2.2 Disubstituted Cobaltoceniums
2.3 Carboxycobaltocenium and Its Derivatives
2.4 Ethynylcobaltocenium and Its Derivatives
2.5 Other Cobaltocenium Derivatives
3 Rhodocenium-Containing Derivatives and Macromolecules
4 Summary and Outlook
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References
- 1a Wilkinson G, Rosenblum M, Whiting MC, Woodward RB. J. Am. Chem. Soc. 1952; 74: 2125
- 1b Pfab W, Fischer EO. Z. Anorg. Allg. Chem. 1953; 274: 316
- 2a Resconi L, Cavallo L, Fait A, Piemontesi F. Chem. Rev. 2000; 100: 1253
- 2b Jutzi P, Burford N In Metallocenes . Wiley-VCH; Weinheim: 2008: 1
- 2c Benedikt GM In Metallocene Technology in Commercial Applications . Benedikt GM. William Andrew Publishing; Norwich, NY: 1999. vi
- 3a Atkinson RC. J, Long NJ In Ferrocenes . John Wiley & Sons; Chichester: 2008: 1
- 3b Moriuchi T, Hirao T. Acc. Chem. Res. 2010; 43: 1040
- 3c Gan K.-S, Hor TS. A In Ferrocenes . Togni A, Hayashi T. Wiley-VCH Verlag GmbH; Weinheim, Germany: 1994
- 3d Foucher DA, Tang BZ, Manners I. J. Am. Chem. Soc. 1992; 114: 6246
- 3e Nguyen P, Gómez-Elipe P, Manners I. Chem. Rev. 1999; 99: 1515
- 3f Zhou J, Whittell GR, Manners I. Macromolecules 2014; 47: 3529
- 4a Hardy CG, Ren L, Zhang J, Tang C. Isr. J. Chem. 2012; 52: 230
- 4b Hardy CG, Zhang J, Yan Y, Ren L, Tang C. Prog. Polym. Sci. 2014; 39: 1742
- 5a Chadha P, Ragogna PJ. Chem. Commun. 2011; 47: 5301
- 5b Hadadpour M, Gwyther J, Manners I, Ragogna PJ. Chem. Mater. 2015; 27: 3430
- 5c Hadadpour M, Liu Y, Chadha P, Ragogna PJ. Macromolecules 2014; 47: 6207
- 5d Yan Y, Zhang J, Tang C In Controlled Radical Polymerization: Materials . Vol. 1188. American Chemical Society; Washington, DC: 2015: 15
- 6 Wilkinson G. J. Am. Chem. Soc. 1952; 74: 6148
- 7a Kemmitt RD. W, Russell DR In Comprehensive Organometallic Chemistry . Wilkinson G, Stone FG. A, Abel EW. Pergamon; Oxford: 1982: 1
- 7b Long NJ. Metallocenes: An Introduction to Sandwich Complexes. Wiley; Oxford, Ox; Malden, MA, USA: 1998
- 8 Andrews CG, Macdonald CL. B. Acta Crystallogr., Sect. E: Struct. Rep. Online 2005; 61: m2103
- 9a Mochida T, Funasako Y, Inagaki T, Li M.-J, Asahara K, Kuwahara D. Chem. Eur. J. 2013; 19: 6257
- 9b Inagaki T, Mochida T, Takahashi M, Kanadani C, Saito T, Kuwahara D. Chem. Eur. J. 2012; 18: 6795
- 10 Konchenko SN, Gritsan NP, Lonchakov AV, Irtegova IG, Mews R, Ovcharenko VI, Radius U, Zibarev AV. Eur. J. Inorg. Chem. 2008; 2008: 3833
- 11 Brasse CC, Englert U, Salzer A, Waffenschmidt H, Wasserscheid P. Organometallics 2000; 19: 3818
- 12 Yu G.-A, Ren Y, Guan J.-T, Lin Y, Liu SH. J. Organomet. Chem. 2007; 692: 3914
- 13 Pagano JK, Sylvester EC, Warnick EP, Dougherty WG, Piro NA, Kassel WS, Nataro C. J. Organomet. Chem. 2014; 750: 107
- 14 Stahl K.-P, Boche G, Massa W. J. Organomet. Chem. 1984; 277: 113
- 15 Philippopoulos AI, Bau R, Poilblanc R, Hadjiliadis N. Inorg. Chem. 1998; 37: 4822
- 16 Hou J.-G, Zhang P, Ye C, Yu T.-G. Acta Crystallogr., Sect. E: Struct. Rep. Online 2007; 63: m2730
- 17 Hou J.-G, Li D.-B, Qiu M.-Z. Acta Crystallogr., Sect. E: Struct. Rep. Online 2008; 64: m927
- 18a Hou J.-G. Acta Crystallogr., Sect. E: Struct. Rep. Online 2010; 66: m218
- 18b Hou J.-G. Acta Crystallogr., Sect. E: Struct. Rep. Online 2011; 67: m1671
- 18c Wu X.-H, Ren Y, Yu G.-A, Liu S.-H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2006; 62: m426
- 19 Guan J.-T, Zhang K.-C, Dai Z.-Q. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009; 65: m960
- 20 Wu X.-H, Guan J.-T, Jin S, Yu G.-A, Meng X.-G, Liu S.-H. Inorg. Chim. Acta 2009; 362: 3484
- 21 Herberich GE, Fischer A, Wiebelhaus D. Organometallics 1996; 15: 3106
- 22 Herberich GE, Englert U, Fischer A, Wiebelhaus D. Organometallics 1998; 17: 4769
- 23 Erben M, Padělková Z, Štěpnička P, Veselý D, Dušek M. Inorg. Chim. Acta 2010; 363: 3365
- 24 Thornberry MP, Slebodnick C, Deck PA, Fronczek FR. Organometallics 2000; 19: 5352
- 25 Gleiter R, Roers R, Rominger F, Nuber B, Hyla-Kryspin I. J. Organomet. Chem. 2000; 610: 80
- 26 Hollandsworth CB, Hollis WG, Slebodnick C, Deck PA. Organometallics 1999; 18: 3610
- 27 Pammer F, Sun Y, Sieger M, Fiedler J, Sarkar B, Thiel WR. Organometallics 2010; 29: 6165
- 28 Bugenhagen BE. C, Brinn L, Prosenc MH. Organometallics 2014; 33: 7015
- 29 Butovskii MV, Englert U, Herberich GE, Koelle U. Eur. J. Inorg. Chem. 2005; 2005: 971
- 30 Komatsuzaki N, Uno M, Shirai K, Tanaka T, Sawada M, Takahashi S. J. Organomet. Chem. 1995; 498: 53
- 31 Gilbert AM, Katz TJ, Geiger WE, Robben MP, Rheingold AL. J. Am. Chem. Soc. 1993; 115: 3199
- 32a Hall CD, Djedovic N. J. Organomet. Chem. 2002; 648: 8
- 32b Beer PD, Drew MG. B, Hodacova J, Stokes SE. J. Chem. Soc., Dalton Trans. 1995; 3447
- 32c Beer PD, Drew MG. B, Hesek D, Chun Nam K. Chem. Commun. (Cambridge) 1997; 107
- 33 Inyushin S, Shafir A, Sheats JE, Minihane M, Whitten CE. Jr, Arnold J. Polyhedron 2004; 23: 2937
- 34 Simon RA, Mallouk TE, Daube KA, Wrighton MS. Inorg. Chem. 1985; 24: 3119
- 35 Braga D, Giaffreda SL, Polito M, Grepioni F. Eur. J. Inorg. Chem. 2005; 2005: 2737
- 36a Pittman CU, Ayers OE, Suryanarayanan B, McManus SP, Sheats JE. Makromol. Chem. 1974; 175: 1427
- 36b Pittman CU, Ayers OE, McManus SP, Sheats JE, Whitten CE. Macromolecules 1971; 4: 360
- 37 Teplyakov MM, Dvorikova RA, Rukhlyada NN, Leonova EV, Petrovskii PV. Makromol. Chem. 1993; 194: 1671
- 38 Ito T, Kenjo T. Bull. Chem. Soc. Jpn. 1968; 41: 614
- 39 Carraher CE, Peterson GF, Sheats JE, Kirsch T. Makromol. Chem. 1974; 175: 3089
- 40 Mayer UF. J, Gilroy JB, O’Hare D, Manners I. J. Am. Chem. Soc. 2009; 131: 10382
- 41 Gilroy JB, Patra SK, Mitchels JM, Winnik MA, Manners I. Angew. Chem. Int. Ed. 2011; 50: 5851
- 42a Ren Y, Wu X.-H, Yu G.-A, Liu S.-H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2006; 62: m151
- 42b Ren Y, Yu G.-A, Liu S.-H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2005; 61: m2714
- 42c Chen Y, Yu G.-A, Meng X.-G, Liu S.-H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2007; 63: m572
- 43 Sheats JE, Rausch MD. J. Org. Chem. 1970; 35: 3245
- 44 Sheats JE, Kirsch T. Synth. React. Inorg. Met.-Org. Chem. 1973; 3: 59
- 45 Neto AF, Borges AD. L, Miller J, Darin VA. Synth. React. Inorg. Met.-Org. Chem. 1997; 27: 1299
- 46a Yan Y, Zhang J, Qiao Y, Tang C. Macromol. Rapid Commun. 2014; 35: 254
- 46b Vanicek S, Kopacka H, Wurst K, Müller T, Schottenberger H, Bildstein B. Organometallics 2014; 33: 1152
- 47a Beer PD, Hesek D, Hodacova J, Stokes SE. J. Chem. Soc., Chem. Commun. 1992; 270
- 47b Beer PD, Drew MG. B, Graydon AR. J. Chem. Soc., Dalton Trans. 1996; 4129
- 47c Beer PD, Graydon AR. J. Organomet. Chem. 1994; 466: 241
- 47d Beer PD, Hesek D, Kingston JE, Smith DK, Stokes SE, Drew MG. B. Organometallics 1995; 14: 3288
- 48a Huesmann H, Förster C, Siebler D, Gasi T, Heinze K. Organometallics 2012; 31: 413
- 48b González B, Cuadrado I, Alonso B, Casado CM, Morán M, Kaifer AE. Organometallics 2002; 21: 3544
- 48c González B, Cuadrado I, Casado CM, Alonso B, Pastor CJ. Organometallics 2000; 19: 5518
- 49 Sakai S, Takayanagi H, Sumimoto N, Fukuzawa S.-I, Fujinami T, Saeki H. Appl. Organomet. Chem. 1990; 4: 35
- 50 Valério C, Ruiz J, Filiaux J.-L, Astruc D. C. R. Acad. Sci., Ser. IIc: Chem. 1999; 2: 79
- 51a Takada K, Díaz DJ, Abruña HD, Cuadrado I, González B, Casado CM, Alonso B, Morán M, Losada J. Chem. Eur. J. 2001; 7: 1109
- 51b Casado CM, González B, Cuadrado I, Alonso B, Morán M, Losada J. Angew. Chem. Int. Ed. 2000; 39: 2135
- 52 Alonso B, Armada PG, Losada J, Cuadrado I, González B, Casado CM. Biosens. Bioelectron. 2004; 19: 1617
- 53 Ornelas C, Ruiz J, Astruc D. Organometallics 2009; 28: 4431
- 54 Astruc D, Ornelas C, Ruiz J. Chem. Eur. J. 2009; 15: 8936
- 55 Sobransingh D, Kaifer AE. Langmuir 2006; 22: 10540
- 56 Gonzalez B, Casado CM, Alonso B, Cuadrado I, Moran M, Wang Y, Kaifer AE. Chem. Commun. (Cambridge) 1998; 2569
- 57a Maurer A, Kraatz H.-B, Metzler-Nolte N. Eur. J. Inorg. Chem. 2005; 2005: 3207
- 57b Gross A, Habig D, Metzler-Nolte N. ChemBioChem 2013; 14: 2472
- 58 van Staveren DR, Weyhermuller T, Metzler-Nolte N. Dalton Trans. 2003; 210
- 59a Noor F, Wüstholz A, Kinscherf R, Metzler-Nolte N. Angew. Chem. Int. Ed. 2005; 44: 2429
- 59b Noor F, Kinscherf R, Bonaterra GA, Walczak S, Wölfl S, Metzler-Nolte N. ChemBioChem 2009; 10: 493
- 60a Chantson JT, Falzacappa MV. V, Crovella S, Metzler-Nolte N. J. Organomet. Chem. 2005; 690: 4564
- 60b Chantson JT, Verga Falzacappa MV, Crovella S, Metzler-Nolte N. ChemMedChem 2006; 1: 1268
- 61 Trzebiatowska-Gusowska M, Gągor A, Coetsee E, Erasmus E, Swart HC, Swarts JC. J. Organomet. Chem. 2013; 745-746: 393
- 62 Swarts JC, Laws D, Geiger WE. Organometallics 2005; 24: 341
- 63 Cuadrado I, Casado CM, Lobete F, Alonso B, González B, Losada J, Amador U. Organometallics 1999; 18: 4960
- 64 Ren L, Hardy CG, Tang C. J. Am. Chem. Soc. 2010; 132: 8874
- 65 Ren L, Zhang J, Hardy CG, Doxie D, Fleming B, Tang C. Macromolecules 2012; 45: 2267
- 66 Ren L, Hardy CG, Tang S, Doxie DB, Hamidi N, Tang C. Macromolecules 2010; 43: 9304
- 67a Zhang J, Ren L, Hardy CG, Tang C. Macromolecules 2012; 45: 6857
- 67b Zhang J, Yan Y, Chance MW, Chen J, Hayat J, Ma S, Tang C. Angew. Chem. Int. Ed. 2013; 52: 13387
- 67c Zhang J, Pellechia PJ, Hayat J, Hardy CG, Tang C. Macromolecules 2013; 46: 1618
- 68a Ren L, Zhang J, Bai X, Hardy CG, Shimizu KD, Tang C. Chem. Sci. 2012; 3: 580
- 68b Ren L, Zhang J, Hardy CG, Ma S, Tang C. Macromol. Rapid Commun. 2012; 33: 510
- 69 Zhang J, Yan J, Pageni P, Yan Y, Wirth A, Chen Y.-P, Qiao Y, Wang Q, Decho AW, Tang C. Sci. Rep. 2015; 5
- 70 Gu S, Wang J, Kaspar RB, Fang Q, Zhang B, Coughlin EB, Yan Y. Sci. Rep. 2015; 5: 11668
- 71 Wildschek M, Rieker C, Jaitner P, Schottenberger H, Schwarzhans KE. J. Organomet. Chem. 1990; 396: 355
- 72 El Murr N. J. Organomet. Chem. 1981; 208: C9
- 73 Diallo AK, Menuel S, Monflier E, Ruiz J, Astruc D. Tetrahedron Lett. 2010; 51: 4617
- 74 Rapakousiou A, Mouche C, Duttine M, Ruiz J, Astruc D. Eur. J. Inorg. Chem. 2012; 2012: 5071
- 75 Rapakousiou A, Wang Y, Belin C, Pinaud N, Ruiz J, Astruc D. Inorg. Chem. 2013; 52: 6685
- 76 Rapakousiou A, Wang Y, Ruiz J, Astruc D. J. Inorg. Organomet. Polym. Mater. 2014; 24: 107
- 77 Wang Y, Latouche C, Rapakousiou A, Lopez C, Ledoux-Rak I, Ruiz J, Saillard J.-Y, Astruc D. Chem. Eur. J. 2014; 20: 8076
- 78 Wang Y, Rapakousiou A, Latouche C, Daran J.-C, Singh A, Ledoux-Rak I, Ruiz J, Saillard J.-Y, Astruc D. Chem. Commun. 2013; 49: 5862
- 79 Wang Y, Rapakousiou A, Ruiz J, Astruc D. Chem. Eur. J. 2014; 20: 11176
- 80 Wang Y, Rapakousiou A, Astruc D. Macromolecules 2014; 47: 3767
- 81 Sheridan MV, Lam K, Geiger WE. J. Am. Chem. Soc. 2013; 135: 2939
- 82 von der Gruen M, Schaefer C, Gleiter R. Organometallics 2003; 22: 2370
- 83 von der Grün M, Gleiter R, Rominger F. Eur. J. Inorg. Chem. 2008; 2008: 2664
- 84 Wolter-Steingrube A, Bugenhagen BE. C, Herrmann C, Heck J. Eur. J. Inorg. Chem. 2014; 2014: 4115
- 85 Barlow S. Inorg. Chem. 2001; 40: 7047
- 86 Laus G, Strasser CE, Holzer M, Wurst K, Pürstinger G, Ongania K.-H, Rauch M, Bonn G, Schottenberger H. Organometallics 2005; 24: 6085
- 87a Jaitner P, Schottenberger H, Gamper S, Obendorf D. J. Organomet. Chem. 1994; 475: 113
- 87b Andre M, Schottenberger H, Tessadri R, Ingram G, Jaitner P, Schwarzhans KE. Chromatographia 1990; 30: 543
- 88 Cotton FA, Whipple RO, Wilkinson G. J. Am. Chem. Soc. 1953; 75: 3586
- 89 Angelici RJ, Fischer EO. J. Am. Chem. Soc. 1963; 85: 3733
- 90 Baghurst DR, Michael D, Mingos P, Watson MJ. J. Organomet. Chem. 1989; 368: C43
- 91 Rapakousiou A, Herrer Jimenez L, Wang Y, Mouche C, Astruc D. Organometallics 2014; 33: 1259
- 92 Forissier K, Ricard L, Carmichael D, Mathey F. Organometallics 2000; 19: 954
- 93 Donovan BT, Hughes RP, Trujillo HA, Rheingold AL. Organometallics 1992; 11: 64
- 94 Donovan-Merkert BT, Clontz CR, Rhinehart LM, Tjiong HI, Carlin CM, Cundari TR, Rheingold AL, Guzei I. Organometallics 1998; 17: 1716
- 95 Philippopoulos AI, Hadjiliadis N, Hart CE, Donnadieu B, McGowan PC, Poilblanc R. Inorg. Chem. 1997; 36: 1842
- 96 Sheats JE, Spink WC, Nabinger RA, Nicol D, Hlatky G. J. Organomet. Chem. 1983; 251: 93
- 97 Yan Y, Deaton TM, Zhang J, He H, Hayat J, Pageni P, Matyjaszewski K, Tang C. Macromolecules 2015; 48: 1644
- 98 Zhang J, Chen YP, Miller KP, Ganewatta MS, Bam M, Yan Y, Nagarkatti M, Decho AW, Tang C. J. Am. Chem. Soc. 2014; 136: 4873