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Multidimensional potential of boron-containing molecules in functional materials

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Abstract

Boron-containing molecular systems have received much attention under theoretical aspects and from the side of synthetic organic chemistry. However, their potential for further applications such as optically interesting effects such as Non-Linear Optics (NLO), medical uses for Boron Neutron Capture Therapy (BNCT), or magnetism has been recognised only fairly recently. Molecular systems containing boron offer particular mechanisms to accommodate unpaired electrons which may result in stable radicals as spin-bearing materials. Among such materials are organoboron compounds in which the prototypical electron deficient (10B, 11B) boron vs. carbon centers can accept and help to delocalise added electrons in a 2-dimensionally conjugated π system. Alternatively, oligoboron clusters BnXn k and the related carboranes or metallacarboranes are capable of adding or losing single electrons to form paramagnetic clusters with 3-dimensionally delocalised spin, according to combined experimental studies and quantum chemical calculations. The unique nuclear properties of 10B are of therapeutic value if their selective transport via appended carbon nanotubes, boron nanotubes, or magnetic nanoparticles can be effected.

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References

  1. Jemmis E D and Jayasree E G 2003 Acc. Chem. Res. 36 816

    Article  CAS  Google Scholar 

  2. Power P P 2003 Chem. Rev. 103 789

    Article  CAS  Google Scholar 

  3. Liu Z and Marder T B 2008 Angew. Chem. Int. Ed. 47 242

    Article  CAS  Google Scholar 

  4. Szwacki N G, Sadrzadeh A and Yakobson B I 2007 Phys. Rev. Lett. 98 166804

    Article  CAS  Google Scholar 

  5. Vinu A, Anandan S, Anad C, Srinivasu P, Ariga K and Mori T 2008 Mic. Meso. Mater. 109 398

    Article  CAS  Google Scholar 

  6. Nagamatsu J, Nakagawa N, Muranaka T, Zenitani Y and Akimitsu J 2001 Nature 410 63

    Article  CAS  Google Scholar 

  7. Köhler J 2001 Angew. Chem. 113 2501; Angew. Chem. Int. Ed. 40 2435

    Article  Google Scholar 

  8. Giles J R M and Roberts B P 1983 J. Chem. Soc. Perkin Trans. 743

  9. Kaim W 1981 Chem. Ber. 114 3789

    Article  CAS  Google Scholar 

  10. Elbing M and Bazan G C 2008 Angew. Chem. Int. Ed. 47 834

    Article  CAS  Google Scholar 

  11. Liu Y, Xu X, Zheng F and Cui Y 2008 Angew. Chem. Int. Ed. 47 4538

    Article  CAS  Google Scholar 

  12. Kaim W, Hosmane N S, Zalis S, Maguire J A and Lipscomb W N 2009 Angew. Chem. Int Ed. 48 5082

    Article  CAS  Google Scholar 

  13. Bock H and Fuss W 1971 Z. Naturforsch., Teil B26 525

    Google Scholar 

  14. Schulz A and Kaim W 1989 Chem. Ber. 122 1863

    Article  CAS  Google Scholar 

  15. Hoffmann R and Lipscomb W N 1962 J. Chem. Phys. 36 2179

    Article  CAS  Google Scholar 

  16. Yamamoto T, Nakai K and Matsumura A 2008 Cancer Lett. 262 143

    Article  CAS  Google Scholar 

  17. Bock H, Kaim W, Semkow A and Nöth H 1980 J. Am. Chem. Soc. 102 4421

    Article  CAS  Google Scholar 

  18. Kaim W and Lubitz W 1983 Angew. Chem. 95 915; Kaim W and Lubitz W 1983 Angew. Chem. Int. Ed. Engl. 22 892; Kaim W and Lubitz W 1983 Angew. Chem. Suppl. 1209

    CAS  Google Scholar 

  19. Lichtblau A, Kaim W, Schulz A and Stahl T 1992 J. Chem. Soc., Perkin Trans. 2 1497

    Google Scholar 

  20. Eisch J J, Dluzniewski T and Behrooz M 1993 Heteroat. Chem. 4 235

    Article  CAS  Google Scholar 

  21. Griffin R G and van Willigen H 1972 J. Chem. Phys. 57 2285

    Google Scholar 

  22. Olmstead M M and Power P P 1086 J. Am. Chem. Soc. 108 4235

    Article  Google Scholar 

  23. Cummings S A, Iimura M, Harlan C J, Kwaan R J, Trieu I V, Norton J R, Bridgewater B M, Jäkle F, Sundararaman A and Tilset M 2006 Organoemetallics 25 1565

    Article  CAS  Google Scholar 

  24. Kaim W and Schulz A 1984 Angew. Chem. Int. Ed. Engl. 23 615

    Article  Google Scholar 

  25. Yuan Z, Collings J C, Taylor N J, Marder T B, Jardin C and Halet J-F 2000 J. Solid State Chem. 154 5

    Article  CAS  Google Scholar 

  26. Pan J-H, Chou Y-M, Chiu H-L and Wang B-C 2007 J. Phys. Org. Chem. 20 743

    Article  CAS  Google Scholar 

  27. Zalis S and Kaim W 2007 Main Group Chem. 6 267

    Google Scholar 

  28. Robin M B and Day P 1967 Adv. Inorg. Chem. Radiochem. 10 247

    Article  CAS  Google Scholar 

  29. Richardson D E and Taube H 1984 Coord. Chem. Rev. 60 107

    Article  CAS  Google Scholar 

  30. Kaim W and Lahiri G K 2007 Angew. Chem. 119 1808; Angew. Chem. Int. Ed. 46 1778

    Article  Google Scholar 

  31. Kaim W and B. Sarkar B 2007 Coord. Chem. Rev. 251 584

    Article  CAS  Google Scholar 

  32. Lambert C, Nöll G and Schelter J 2002 Nature Mat. 1 69

    Article  CAS  Google Scholar 

  33. Bonvoisin J, Launay J-P, Rovira C and Veciana J 1994 Angew. Chem. Int. Ed. Engl. 33 2106

    Article  Google Scholar 

  34. Rajca A, Rajca S and Desai S R 1995 Chem. Commun. 25

  35. Hoefelmeier J D and Gabbai F P 2000 J. Am. Chem. Soc. 122 9054

    Article  CAS  Google Scholar 

  36. Klusik H and Berndt A 1982 J. Organomet. Chem. 232 C21

    Article  CAS  Google Scholar 

  37. Grigsby W J and Power P P 1997 Chem. Eur. J. 3 368

    Article  CAS  Google Scholar 

  38. Lichtblau A, Hausen H-D, Schwarz W and Kaim W 1993 Inorg. Chem. 32 73

    Article  CAS  Google Scholar 

  39. Abbey E R, Zakharov L N and Liu S-Y 2008 J. Am. Chem. Soc. 130 7250

    Article  CAS  Google Scholar 

  40. Kaim W 1994 Top. Curr. Chem. 169 231

    CAS  Google Scholar 

  41. Hausen H-D, Schulz A and Kaim W 1988 Chem. Ber. 121 2059

    Article  CAS  Google Scholar 

  42. Summers L A 1980 The bipyridinium herbicides (London: Academic Press)

    Google Scholar 

  43. Fossey J, Lefort D and Sorba J 1995 Free radicals in organic chemistry (New York: Wiley)

    Google Scholar 

  44. von Ragué Schleyer P 2005 Chem. Rev. 105 3433

    Article  CAS  Google Scholar 

  45. Kadish K M and Ruoff R S 2000 Fullerenes: Chemistry, physics, and technology (New York: Wiley)

    Google Scholar 

  46. Lewis J S and Kaczmarczyk A 1966 J. Am. Chem. Soc. 88 1068

    Article  CAS  Google Scholar 

  47. Klanberg F, Eaton D R, Guggenberger L J and Muetterties E L 1967 Inorg. Chem. 6 1271

    Article  CAS  Google Scholar 

  48. McKee M L, Wang Z-X and von Ragué Schleyer P 2000 J. Am. Chem. Soc. 122 4781

    Article  CAS  Google Scholar 

  49. McKee M L 2002 Inorg. Chem. 41 1299

    Article  CAS  Google Scholar 

  50. Heinrich A, Keller H-L and Preetz W 1990 Z. Naturforsch. B45 184

    Google Scholar 

  51. Lorenzen V and Preetz W 1997 Z. Naturforsch. 52 565

    CAS  Google Scholar 

  52. Lorenzen V, Preetz W, Baumann F and Kaim W 1998 Inorg. Chem. 37 4011

    Article  CAS  Google Scholar 

  53. Wanner M, Kaim W, Lorenzen V and Preetz W 1999 Z. Naturforsch. B54 1103

    Google Scholar 

  54. Speiser B, Wizemann T and Wuerde M 2003 Inorg. Chem. 42 4018

    Article  CAS  Google Scholar 

  55. Einholz W, Vaas K, Wieloch C, Speiser B, Wizemann T, Stroebele M and Meyer H-J 2002 Z. Anorg. Allg. Chem. 628 258

    Article  CAS  Google Scholar 

  56. Wong E H and Kabbani R M 1981 Inorg. Chem. 19 451

    Article  Google Scholar 

  57. Speiser B, Tittel C, Einholz W and Schäfer R 1999 Dalton Trans. 1741

  58. Binder H, Kellner R, Vaas K, Hein M, Baumann F, Wanner M, Winter R, Kaim W, Hönle W, Grin Y, Wedig U, Schultheiss M, Kremer R K, von Schnering H G, Groeger O and Engelhardt G 1999 Z. Anorg. Allg. Chem. 625 1059

    Article  CAS  Google Scholar 

  59. Binder H, Kellner R, Vaas K, Hein M, Baumann F, Wanner M, Kaim W, Wedig U, Hönle W, von Schnering H G, Groeger O and Engelhardt G 1999 Z. Anorg. Allg. Chem. 625 1638

    Article  CAS  Google Scholar 

  60. Peymann T, Knobler C B, Khan S I and Hawthorne M F 2001 Inorg. Chem. 40 1291

    Article  CAS  Google Scholar 

  61. Farha O K, Julius R L, Lee M W, Huertas R E, Knobler C B and Hawthorne M F 2005 J. Am. Chem. Soc. 127 18243

    Article  CAS  Google Scholar 

  62. Lee W W, Farha O K, Hawthorne M F and Hansch C H 2007 Angew. Chem. Int. Ed. 46 3018

    Article  CAS  Google Scholar 

  63. Van N-D, Tiritiris I, Schleid Th, Sarkar B, Kaim W and Winter R (to be submitted)

  64. Fowler P W 1986 J. Chem. Soc., Faraday Trans. 2 82 61

    Google Scholar 

  65. Kaim W, Bock H, Hawker P and Timms P L 1980 J. Chem. Soc. Chem. Commun. 577

  66. Volkov O and Paetzold P 2006 Z. Anorg. Allg. Chem. 632 945

    Article  CAS  Google Scholar 

  67. King B T, Noll B C, McKinley A J and Mich J 1996 J. Am. Chem. Soc. 118 10902

    Article  CAS  Google Scholar 

  68. Fox M A, Nervi C, Crivello A and Low P J 2007 Chem. Commun. 2372

  69. Fu X, Chan H-S and Xie Z 2007 J. Am. Chem. Soc. 129 8964

    Article  CAS  Google Scholar 

  70. Hosmane N S, Zhang H, Maguire J A, Wang Y, Demissie T, Colacort T J, Ezhova M B, Lu K-J, Zhu D, Gray T G, Helfert S C, Hosmane S N, Collins J D, Baumann F, Kaim W and Lipscomb W N 2000 Organometallics 19 497

    Article  CAS  Google Scholar 

  71. Hosmane N S, Zhang H, Maguire J A, Wang Y, Colacot T J and Gray T G 1996 Angew. Chem., Int. Ed. Engl. 35 1000

    Article  CAS  Google Scholar 

  72. Lipscomb W N, Pitochelli A R and Hawthorne M F 1959 J. Am. Chem. Soc. 81 5833

    Article  CAS  Google Scholar 

  73. Chen Z and King R B 2005 Chem. Rev. 105 3613

    Article  CAS  Google Scholar 

  74. Iijma S 1991 Nature 354 56

    Article  Google Scholar 

  75. Cuenca A, Jiang H, Hochwald S, Delano M, Cance W and Grobmyer S 2006 Cancer 107 459

    Article  CAS  Google Scholar 

  76. Pantarotto D, Briand J P, Prato M and Bianco A 2004 Chem. Commun. 1 16

    Article  CAS  Google Scholar 

  77. Cherukuri P, Bachilo S M, Litovsky S H and Weisman R B 2004 J. Am. Chem. Soc. 126 15638

    Article  CAS  Google Scholar 

  78. Kam N W, O’Connell M, Wisdom J A and Dai H 2005 Proc. Natl. Acad. Sci. USA 102 11600

    Article  CAS  Google Scholar 

  79. Pantarotto D, Partidos C D, Graff R, Hoebeke J, Briand J-P, Prato M and Bianco A 2003 J. Am. Chem. Soc. 125 6160

    Article  CAS  Google Scholar 

  80. Kam N WS, Jessop T C, Wender P A and Dai H 2004 J. Am. Chem. Soc. 126 6850

    Article  CAS  Google Scholar 

  81. Furtado C A, Kim U J, Gutierrez H R, Pan L, Dickey E C and Eklund P C 2004 J. Am. Chem. Soc. 126 6095

    Article  CAS  Google Scholar 

  82. Hu H, Ni Y, Montana V, Haddon R C and Parpura V 2004 Nano Lett. 4 507

    Article  CAS  Google Scholar 

  83. Georgakilas V, Tagmatarchis N, Pantarotto D, Bianco A, Briand J P and Prato M 2002 Chem. Commun. 24 3050

    Article  CAS  Google Scholar 

  84. Fu K, Li H, Zhou B, Kitaygorodskiy A, Allard L F and Sun Y P 2004 J. Am. Chem. Soc. 126 4669

    Article  CAS  Google Scholar 

  85. Georgakilas V, Kordatos K, Prato M, Guldi D M, Holzinger M and Hirsch A 2002 J. Am. Chem. Soc. 124 760

    Article  CAS  Google Scholar 

  86. Guldi D M, Marcaccio M, Paolucci D, Paolucci F, Tagmatarchis N, Tasis D, Vazquez E and Prato M 2003 Angew. Chem. Int. Ed. 42 4206

    Article  CAS  Google Scholar 

  87. Holzinger M, Abraham J, Whelan P, Graupner, R, Ley, L, Hennrich F, Kappes M and Hirsch A 2003 J. Am. Chem. Soc. 125 8566

    Article  CAS  Google Scholar 

  88. Sun Y P, Huang W, Lin Y, Fu K, Kitaygorodskiy A, Riddle L A, Yu Y J and Carroll D L 2001 Chem. Mater. 13 2864

    Article  CAS  Google Scholar 

  89. Peng H, Alemany L B, Margrave J L and Khabashesku V N 2003 J. Am. Chem. Soc. 125 15174

    Article  CAS  Google Scholar 

  90. Peng H, Reverdy P, Khabashesku V N and Margrave J L 2003 Chem. Commun. 3 362

    Article  CAS  Google Scholar 

  91. Huang W, Fernando S, Lin Y, Zhou B, Allard L F and Sun Y P 2003 Langmuir 19 7084

    Article  CAS  Google Scholar 

  92. Dyke C A and Tour J M 2003 Nano Lett. 3 1215

    Article  CAS  Google Scholar 

  93. Zhu W, Minami N, Kazaoui S and Kim Y. 2003 J. Mater. Chem. 13 2196

    Article  CAS  Google Scholar 

  94. Umek P, Seo J W, Hernadi K, Mrzel A, Pechy Peter, Mihailovic D D and Forro L 2003 Chem. Mater. 15 4751

    Article  CAS  Google Scholar 

  95. Hu H, Zhao B, Hamon M A, Kamaras K, Itkis M E and Haddon R C 2003 J. Am. Chem. Soc. 125 14893

    Article  CAS  Google Scholar 

  96. Chen R J, Choi H C, Bangsaruntip S, Yenilmez E, Tang X, Wang Q, Chang Y-L and Dai H 2004 J. Am. Chem. Soc. 126 1563

    Article  CAS  Google Scholar 

  97. Zhu Y H, Ang T P, Carpenter K, Maguire J, Hosmane N and Takagaki M.2005 J. Am. Chem. Soc. 127 9875

    Article  CAS  Google Scholar 

  98. Dai H 2002 Acc. Chem. Res. 35 1035

    Article  CAS  Google Scholar 

  99. Morgan D A, Sloan J and Green M L H 2002 Chem. Commun. 20 2442

    Article  CAS  Google Scholar 

  100. Xu T, Zheng J G, Wu N, Nicholls A, Roth J R, Dikin D A and Ruoff R S 2004 Nano Lett. 4 963

    Article  CAS  Google Scholar 

  101. Cao L M, Tian H, Zhang Z, Zhang X Y, Gao C X and Wang W K 2004 Nanotechnology 15 139

    Article  CAS  Google Scholar 

  102. Ciuparu D, Klie R, Zhu Y and Pfefferle L 2004 J. Phys. Chem. 108 3967

    CAS  Google Scholar 

  103. Kuntsmann J and Quandt A 2005 Chem. Phys. Lett. 402 21

    Article  CAS  Google Scholar 

  104. Quandt A and Boustani I 2005 Chem. Phys. Chem. 6 2001

    CAS  Google Scholar 

  105. Alexiou C, Arnold W, Klein R J, Parak F G, Hulin P, Bergemann C, Erhardt W, Wagenpfeil S and Lübbe A S 2000 Cancer Res. 60 6641

    CAS  Google Scholar 

  106. Pulfer S K, Ciccotto S L and Gallo J M 1999 J. Neuro-Oncol. 41 99

    Article  CAS  Google Scholar 

  107. Sincai M, Ganga D, Ganga M, Argherie D and Bica D 2005 J. Magn. Magn. Mater. 293 438

    Article  CAS  Google Scholar 

  108. Gallo J M and Hafeli U 1997 Cancer Res. 57 3063

    CAS  Google Scholar 

  109. Veyret R, Delair T and Elaissari A 2005 J. Magn. Magn. Mater. 293 171

    Article  CAS  Google Scholar 

  110. Sang J S, Reichel J, Bo H, Schuchman M and Sang B L 2005 J. Am. Chem. Soc. 127 7316

    Article  CAS  Google Scholar 

  111. Zebli B, Susha A S, Sukhorukov G B, Rogach A L and Parak W J 2005 Langmuir 21 4262

    Article  CAS  Google Scholar 

  112. Zhu Y H Bis(aminoalkyl)-dicarbaborane derived boron neutral capture therapy drugs, US Patent Application number 60/737,827, filed on 17 November 2005

  113. Zhu Y H (unpublished results)

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Kaim, W., Hosmane, N.S. Multidimensional potential of boron-containing molecules in functional materials. J Chem Sci 122, 7–18 (2010). https://doi.org/10.1007/s12039-010-0008-9

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