Abstract
The impact of hydroxyl group adsorption on fullerene surface (namely fullerenol) has been systematically investigated in this study using the hybrid density-functional theory calculations. We find that the relative stability of fullerenol clearly depends on the distribution of hydroxyl group on the surface. The eight hydroxyl groups in C20(OH)8 structure show preference to accumulate on two adjoining five-numbered rings. Analysis of reaction energy indicates that the formation of fullerenol from the C20 fullerene and hydroxyl group is energetically favorable. The highly hydroxylated fullerene is found to have high kinetic stability and low chemical reactivity, which is mostly associated with its electron distribution of HOMO and LUMO orbitals. In addition, the electronic structure of the most stable fullerenols has been analyzed by means of the total and partial density of states.
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Kroto HW, Heath JR, OflBrien SC, Curl RF, Smalley RE (1985) Nature 318:162–163
Qiao R, Roberts AP, Mount AS, Klaine SJ, Ke PC (2007) Nano Lett 7:614–619
Mateo-Alonso A, Iliopoulos K, Couris S, Prato M (2008) J Am Chem Soc 130:1534–1535
Nagase S, Kobayashi T, Akasaka T, Wakahara T (2000) Fullerenes: chemistry, physics and technology, Chapt 9. In: Nagase S et al. (ed) Endohedral metallofullerenes: theory, electrochemistry, and chemical reactions. Wiley, New York, pp. 395–429
Akasaka T, Nagase S (2002) Endofullerenes: a new family of carbon clusters. Kluwer Academic Publisher, Dordrecht
Baowan D, Cox BJ, Hill JM (2012) J Mol Model 18:549–557
Iohara D, Hirayama F, Higashi K, Yamamoto K, Uekama K (2011) Mol Pharm 8:1276–1284
Xu A, Chai Y, Nohmi T, Hei TK (2009) Part Fibre Toxicol 6:3–13
Bal R, Türk G, Tuzcu M, Yilmaz O, Ozercan I, Kuloglu T, Gür S, Nedzvetsky VS, Tykhomyrov AA, Andrievskyg GV, Baydas G, Naziroglu M (2011) Toxicology 282:69–81
Bosi S, Ros TD, Spalluto G, Prato M (2003) Eur J Med Chem 38:913–923
Sofou P, Elemes Y, Panou-Pomonis E, Stavrakoudis A, Tsikaris V, Sakarellos C, Sakarellos-Daitsiotis M, Maggini M, Formaggiob F, Toniolo C (2004) Tetrahedron 60:2823–2828
Chen Z, Ma K, Wang G, Zhao X, Tang A (2000) Comp Theor Chem 498:227–232
Jacevic V, Djordjevic-Milic V, Dragojevic-Simic V, Radic N, Govedarica B, Dobric S, Srdjenovic B, Injac R, Djordjevic A, Vasovic V (2007) Toxicol Lett 172:S146
Badireddy AR, Hotze EM, Chellam S, Alvarez P, Wiesner MR (2007) Environ Sci Technol 41:6627–6632
Guirado-López RA, Rincón ME (2006) J Chem Phys 125:154310–154312
Vileno B, Marcoux PR, Lekka M, Sienkiewicz A, Fehér T, Forró L (2006) Adv Funct Mater 16:120–128
Isakovic A, Markovic Z, Todorovic-Markovic B, Nikolic N, Vranjes-Djuric S, Mirkovic M, Dramicanin M, Harhaji L, Raicevic N, Nikolic Z, Trajkovic V (2006) Toxicol Sci 91:173–183
Sayes CM, Fortner JD, Guo W, Lyon D, Boyd AM, Ausman KD, Tao YJ, Sitharaman B, Wilson LJ, Hughes JB, West JL, Colvin VL (2004) Nano Lett 4:1881–1887
Srdjenovic B, Milic-Torres V, Grujic N, Stankov K, Djordjevic A, Vasovic V (2010) Toxicol Mech Method 20:298–305
Bogdanovića G, Kojića V, Đorđevićb A, Čanadanović-Brunetc J, Vojinović-Miloradovb M, Baltić VV (2004) Toxicol In Vitro 18:629–637
Lu L-H, Lee Y-T, Chen H-W, Chiang LY, Huang H-C (1998) Br J Pharmacol 123:1097–1102
Kojić V, Jakimov D, Bogdanović G, Djordjević A (2005) Mater Sci Forum 494:543–548
Xu J-Y, Li Q-N, Li J-G, Ran T-C, Wu S-W, Song W-M, Chen S-L, Li W-X (2007) Carbon 45:1865–1870
Xu J-Y, Han K, Li S-X, Cheng J-S, Xu G-T, Li W-X, Li Q-N (2009) J Appl Toxicol 29:578–584
Fileti EE, Rivelino R, Mota FdB, Malaspina T (2008) Nanotechnology 19:365703–365707
Zhang G, Liu Y, Liang D, Gan L, Li Y (2010) Angew Chem Int Ed 49:5293–5295
Cohen AJ, Mori-Sanchez P, Yang W (2012) Chem Rev 112:289–320
Sabirov DS, Tukhbatullina AA, Bulgakov RG (2012) Comp Theor Chem 993:113–117
He H, Zheng L, Jin P, Yang M (2011) Comp Theor Chem 974:16–20
Li X-J, Zhong Z-J, Wu H-Z (2011) J Mol Model 17:2623–2630
Fileti EE, Rivelino R (2009) Chem Phys Lett 467:339–343
Rodríguez-Zavala JG, Guirado-López RA (2006) J Phys Chem A 110:9459–9468
Wang B-C, Wang H-W, Tso H-C, Chen T-L, Chou Y-M (2002) J Mol Struct (Theochem) 581:177–186
Rodríguez-Zavalaa JG, Tenorioa FJ, Samaniegoa C, Méndez-Barrientosa CI, Peña-Leconaa FG, Muñoz-Maciela J, Flores-Morenob R (2011) Mol Phys 109:1771–1783
Prinzbach H, Weiler A, Landenberger P, Wahl F, Worth J, Scott LT, Gelmont M, Olevano D, Issendorff Bv (2000) Nature 407:60–63
Scuseria GE (1996) Science 271:942–945
Ashrafi AR (2005) Chem Phys Lett 406:75–80
Devos A, Lannoo M (1998) Phys Rev B 58:8236–8239
Miyamoto Y, Saito M (2001) Phys Rev B 63:161401–161404
Becke AD (1988) Phys Rev A 38:3098–3100
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789
Lu J, Re S, Choe Y-K, Nagase S, Zhou Y, Han R, Peng L, Zhang X, Zhao X (2003) Phys Rev B 67:125415–125417
Leszczynski J, Yanov I (1999) J Phys Chem A 103:396–401
Takahashi T, Suzuki S, Morikawa T, Katayama-Yoshida H, Hasegawa S, Inokuchi H, Seki K, Kikuchi K, Suzuki S, Ikemoto K, Achiba Y (1992) Phys Rev Lett 68:1232–1235
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J, J. A., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A. 02. Gaussian, Inc., Wallingford
O’Boyle NM, Tenderholt AL, Langner KM (2008) J Comp Chem 29:839–845
Zhang C, Sun W, Cao Z (2007) J Chem Phys 126:144306–144307
Xing G, Zhang J, Zhao Y, Tang J, Zhang B, Gao X, Yuan H, Qu L, Cao W, Chai Z, Ibrahim K, Su R (2004) J Phys Chem B 108:11473–11479
Mulliken RS (1955) J Chem Phys 23:1833–1838
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Li, XJ., Yang, XH., Song, LM. et al. A DFT study on structure, stability, and optical property of fullerenols. Struct Chem 24, 1185–1192 (2013). https://doi.org/10.1007/s11224-012-0137-5
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DOI: https://doi.org/10.1007/s11224-012-0137-5