Abstract
Molecular propellers based upon the twisting of a disulfide bond are analyzed here as the locomotion source for fullerene nanoparticles. The HC(CCHSSHCC)3CH and related HC(CCHSSNC)3CH bicyclic compounds are optimized and linked to pyracyclene functioning as a model fullerene surface. It is shown that steric hinderance from the hydrogen atoms on both the bottom of the propeller blade and the linker to the fullerene surface can have significant effects on the rotational potential energy surface. Replacing the bottom CH groups on the molecular propeller with nitrogen atoms not only reduces these barriers significantly, but this action creates a strongly dipolar molecule in HC(CCHSSNC)3CH. Such a system would be responsive to and controllable with an external, rotating, magnetic or electric field. Endohedral fullerenes have known applications for targeted delivery, especially in nanomedicine. Providing further control with molecular propellers could enhance the feasibility and use of these technologies.
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Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) Nature 318:162
Kroto HW (1987) Nature 329:529
Terrones M, Hsu WK, Kroto HW, Walton DRM (1999). In: Hirsch A (ed) Fullerenes and related structures. Springer, Berlin, pp 189–234
Wu M, Pei Y, Dai J, Li H, Zeng XC (2012) J Phys Chem C 116:11378
Schamel D, Mark AG, Gibbs JG, Miksch C, Morozov KI, Leshansky AM, Fischer P (2014) ACS Nano 8:8794
Kottas GS, Clarke LI, Horinek D, Michl J (2005) Chem Rev 105:1281
Vicario J, Walko M, Meetsma A, Feringa BL (2006) J Am Chem Soc 128:5127
Michl J, Sykes CH (2009) ACS Nano 3:1042
Prokop A, Vacek J, Michl J (2012) ACS Nano 6:1901
Kudernac T, Ruangsupapichat N, Parschau M, Maciá B., Katsonis N, Harutyunyan SR, Ernst KH, Feringa BL (2011) Nature 479:208
Vacek J, Michl J (2001) Proc Natl Acad Sci 98:5481
Colledge JJ, Warlow B (2010) Ships of the Royal Navy: a complete record of all fighting ships of the Royal Navy from the 15th century to the present., 4th edn. PA, Casemate, Havertown
Frantz DK, Linden A, Baldridge KK, Siegel JS (2012) J Am Chem Soc 134:1528
Fortenberry RC (2016) RSC Adv 6:43509
Fillmore HL, Shultz MD, Henderson SC, Cooper P, Broaddus WC, Chen ZJ, Shu CY, Zhang J, Ge J, Dorn HC, Corwin F, Hirsch JI, Wilson J, Fatouros PP (2011) Nanomedicine 6:449
Zhang J, Stevenson S, Dorn HC (2013) Acc Chem Res 46:1548
Wilhelm S, Tavares AJ, Dai Q, Ohta S, Audet J, Dvorak HF, Chan WCW (2016) Nature Rev Mat 1:16014
Beyers R, Kiang CH, Johnson RD, Salem JR, DeVries MS, Yannoni CS, Bethune DS, Dorn HC, Burbank P, Harich K, Stevenson S (1994) Nature 370:196
Rubin Y (1999). In: Hirsch A (ed) Fullerenes and related structures. Springer, Berlin, pp 67–91
Herzog U, Rheinwald G (2001) Organometallics 20:5369
Zhou Z, Sarova GH, Zhang S, Ou Z, Tat FT, Kadish KM, Echegoyen L, Guldi DM, Schuster DI, Wilson SR (2006) Chem Eur J 12:4241
Lebedeva MA, Chamberlain TW, Khlobystov AN (2015) Chem Rev 115:11301
Werner HJ, Manby FR, Knowles PJ (2003) J Chem Phys 118:8149
Møller C, Plesset MS (1934) Phys Rev 46:618
Fortenberry RC (2016) New J Chem 40:8149
Hehre WJ, Ditchfeld R, Pople JA (1972) J Chem Phys 56:2257
Sherrill CD (2011) Rev Comput Chem 26:1
Zheng J, Zhao Y, Truhlar DG (2009) J Chem Theory Comput 5:808
Turney JM, Simmonett AC, Parrish RM, Hohenstein EG, Evangelista FA, Fermann JT, Mintz BJ, Burns LA, Wilke JJ, Abrams ML, Russ NJ, Leininger ML, Janssen CL, Seidl ET, Allen WD, Schaefer III HF, King RA, Valeev EF, Sherrill CD, Crawford TD (2012) Wiley Interdiscip Rev: Comput Mol Sci 2(4): 556
Schmidt JR, Polik WF (2013) WebMO Enterprise, version 13.0; WebMO LLC: Holland, MI, USA. http://www.webmo.net
Lomas JS, Adenier A (2002) J Chem Soc, Perkin Trans 2:1051
Fortenberry RC, Francisco JS (2017) Astrophys J 835:243
Shigemitsu Y, Kaneko M, Tajima Y, Takeuchi K (2004) Chem Lett 33:1604
Theis ML, Candian A, Tielens AGGM, Lee TJ, Fortenberry RC (2015) Phys Chem Chem Phys 17:14761
Fortenberry RC, Moore MM, Lee TJ (2016) J Phys Chem A 120:7327
Acknowledgments
Georgia Southern University is thanked for the start-up funds and computer hardware/software necessary to perform this research. Additionally, the WebMO graphical user interface [30] was utilized in the production of the molecules given in the figures.
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Hurst, M.O., Fortenberry, R.C. Two small molecular propellers and their rotational potential energy surfaces. Struct Chem 28, 1653–1662 (2017). https://doi.org/10.1007/s11224-017-0931-1
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DOI: https://doi.org/10.1007/s11224-017-0931-1