Nanocar

For other nanocars, see Nanocar Race.
Nanocar with C60 fullerene wheels[1]
Chemical structure of a nanocar. The wheels are C60 fullerene molecules.
Names
Preferred IUPAC name
74,165-Bis[(2,5-bis(decyloxy)-4-{[(C60-Ih)[5,6]fulleren-1(9H)-yl]ethynyl}phenyl)ethynyl]-42,45,102,105,132,135,192,195-octakis(decyloxy)-19H,229H-1,22(1)-di(C60-Ih)[5,6]fullerena-4,10,13,19(1,4),7,16(1,2)-hexabenzenadodecaphane-2,5,8,11,14,17,20-heptayne
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C430H274O12/c1-13-25-37-49-61-73-85-97-135-431-179-153-173(181(433-137-99-87-75-63-51-39-27-15-3)151-171(179)123-119-165-147-161(111-115-167-149-187(439-143-105-93-81-69-57-45-33-21-9)175(157-183(167)435-139-101-89-77-65-53-41-29-17-5)127-131-427-415-399-375-319-287-255-207-195-191-196-208(207)256-264-248-224(196)232-216-203(191)215-231-223(195)247-263(255)311(319)343-335-279(247)271(231)303-295-239(215)240(216)296-304-272(232)280(248)336-344-312(264)320(288(256)287)376(375)400(415)384(344)392-360(336)352(304)368-328(296)327(295)367-351(303)359(335)391(383(343)399)419(427)407(367)408(368)420(392)427)109-113-163(165)117-121-169-155-189(441-145-107-95-83-71-59-47-35-23-11)177(159-185(169)437-141-103-91-79-67-55-43-31-19-7)129-133-429-417-403-379-323-291-259-211-199-193-200-212(211)260-268-252-228(200)236-220-205(193)219-235-227(199)251-267(259)315(323)347-339-283(251)275(235)307-299-243(219)244(220)300-308-276(236)284(252)340-348-316(268)324(292(260)291)380(379)404(417)388(348)396-364(340)356(308)372-332(300)331(299)371-355(307)363(339)395(387(347)403)423(429)411(371)412(372)424(396)429)125-126-174-154-180(432-136-98-86-74-62-50-38-26-14-2)172(152-182(174)434-138-100-88-76-64-52-40-28-16-4)124-120-166-148-162(112-116-168-150-188(440-144-106-94-82-70-58-46-34-22-10)176(158-184(168)436-140-102-90-78-66-54-42-30-18-6)128-132-428-416-401-377-321-289-257-209-197-192-198-210(209)258-266-250-226(198)234-218-204(192)217-233-225(197)249-265(257)313(321)345-337-281(249)273(233)305-297-241(217)242(218)298-306-274(234)282(250)338-346-314(266)322(290(258)289)378(377)402(416)386(346)394-362(338)354(306)370-330(298)329(297)369-353(305)361(337)393(385(345)401)421(428)409(369)410(370)422(394)428)110-114-164(166)118-122-170-156-190(442-146-108-96-84-72-60-48-36-24-12)178(160-186(170)438-142-104-92-80-68-56-44-32-20-8)130-134-430-418-405-381-325-293-261-213-201-194-202-214(213)262-270-254-230(202)238-222-206(194)221-237-229(201)253-269(261)317(325)349-341-285(253)277(237)309-301-245(221)246(222)302-310-278(238)286(254)342-350-318(270)326(294(262)293)382(381)406(418)390(350)398-366(342)358(310)374-334(302)333(301)373-357(309)365(341)397(389(349)405)425(430)413(373)414(374)426(398)430/h109-110,113-114,147-160,415-418H,13-108,135-146H2,1-12H3/t415-,416-,417-,418-,427+,428+,429+,430+
    Key: XMCLKYABXSBFLO-GAVGUPCASA-N
  • Nanocar core structure: InChI=1S/C310H34/c1(53-3-7-59(8-4-53)33-41-69-51-65(29-27-55-11-19-61(20-12-55)43-47-307-295-279-255-199-167-135-87-75-71-76-88(87)136-144-128-104(76)112-96-83(71)95-111-103(75)127-143(135)191(199)223-215-159(127)151(111)183-175-119(95)120(96)176-184-152(112)160(128)216-224-192(144)200(168(136)167)256(255)280(295)264(224)272-240(216)232(184)248-208(176)207(175)247-231(183)239(215)271(263(223)279)299(307)287(247)288(248)300(272)307)35-39-67(69)37-31-57-15-23-63(24-16-57)45-49-309-297-283-259-203-171-139-91-79-73-80-92(91)140-148-132-108(80)116-100-85(73)99-115-107(79)131-147(139)195(203)227-219-163(131)155(115)187-179-123(99)124(100)180-188-156(116)164(132)220-228-196(148)204(172(140)171)260(259)284(297)268(228)276-244(220)236(188)252-212(180)211(179)251-235(187)243(219)275(267(227)283)303(309)291(251)292(252)304(276)309)2-54-5-9-60(10-6-54)34-42-70-52-66(30-28-56-13-21-62(22-14-56)44-48-308-296-281-257-201-169-137-89-77-72-78-90(89)138-146-130-106(78)114-98-84(72)97-113-105(77)129-145(137)193(201)225-217-161(129)153(113)185-177-121(97)122(98)178-186-154(114)162(130)218-226-194(146)202(170(138)169)258(257)282(296)266(226)274-242(218)234(186)250-210(178)209(177)249-233(185)241(217)273(265(225)281)301(308)289(249)290(250)302(274)308)36-40-68(70)38-32-58-17-25-64(26-18-58)46-50-310-298-285-261-205-173-141-93-81-74-82-94(93)142-150-134-110(82)118-102-86(74)101-117-109(81)133-149(141)197(205)229-221-165(133)157(117)189-181-125(101)126(102)182-190-158(118)166(134)222-230-198(150)206(174(142)173)262(261)286(298)270(230)278-246(222)238(190)254-214(182)213(181)253-237(189)245(221)277(269(229)285)305(310)293(253)294(254)306(278)310/h3-26,35-36,39-40,51-52,295-298H/t295-,296-,297-,298-,307+,308+,309+,310+
    Key: WQLDMLHCQIDOPH-BTRKRKDISA-N
  • Nanocar with alkyl sidechains: CCCCCCCCCCOc1cc(c(cc1C#Cc2cc(ccc2C#Cc3cc(c(cc3OCCCCCCCCCC)C#CC45c6c7c8c9c1c2c3c%10c%11c%12c%13c3c1c1c8c3c6c6c4c4c8c%14c%15c%16c(c%11c%11c%10c%10c2c2c9c7c7c9c2c%10c2c%11c%16c%10c2c9c(c4c%10%14)C57)c2c%12c4c%13c1c3c1c4c(c2%15)c8c16)OCCCCCCCCCC)C#Cc1cc(c(cc1OCCCCCCCCCC)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43)OCCCCCCCCCC)OCCCCCCCCCC)C#Cc1cc(c(cc1OCCCCCCCCCC)C#Cc1cc(ccc1C#Cc1cc(c(cc1OCCCCCCCCCC)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43)OCCCCCCCCCC)C#Cc1cc(c(cc1OCCCCCCCCCC)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43)OCCCCCCCCCC)OCCCCCCCCCC
  • Nanocar core structure: c1cc(ccc1C#Cc2ccc(cc2)C#Cc3cc(ccc3C#Cc4ccc(cc4)C#CC56c7c8c9c1c2c3c4c%10c%11c%12c%13c4c2c2c9c4c7c7c5c5c9c%14c%15c%16c(c%11c%11c%10c%10c3c3c1c8c1c8c3c%10c3c%11c%16c%10c3c8c(c5c%10%14)C61)c1c%12c3c%13c2c4c2c3c(c1%15)c9c27)C#Cc1ccc(cc1)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43)C#Cc1cc(ccc1C#Cc1ccc(cc1)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43)C#Cc1ccc(cc1)C#CC12c3c4c5c6c7c8c9c%10c%11c%12c%13c9c7c7c5c5c3c3c1c1c9c%14c%15c%16c(c%11c%11c%10c%10c8c8c6c4c4c6c8c%10c8c%11c%16c%10c8c6c(c1c%10%14)C24)c1c%12c2c%13c7c5c4c2c(c1%15)c9c43
Properties
C430H274O12
Molar mass 5632.769
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The nanocar is a molecule designed in 2005 at Rice University by a group headed by Professor James Tour. Despite the name, the original nanocar does not contain a molecular motor, hence, it is not really a car. Rather, it was designed to answer the question of how fullerenes move about on metal surfaces; specifically, whether they roll or slide (they roll).

The molecule consists of an H-shaped 'chassis' with fullerene groups attached at the four corners to act as wheels.

When dispersed on a gold surface, the molecules attach themselves to the surface via their fullerene groups and are detected via scanning tunneling microscopy. One can deduce their orientation as the frame length is a little shorter than its width.

Upon heating the surface to 200 °C the molecules move forward and back as they roll on their fullerene "wheels". The nanocar is able to roll about because the fullerene wheel is fitted to the alkyne "axle" through a carbon-carbon single bond. The hydrogen on the neighboring carbon is no great obstacle to free rotation. When the temperature is high enough, the four carbon-carbon bonds rotate and the car rolls about. Occasionally the direction of movement changes as the molecule pivots. The rolling action was confirmed by Professor Kevin Kelly, also at Rice, by pulling the molecule with the tip of the STM.

  1. ^ Shirai, Y.; et al. (2005). "Directional Control in Thermally Driven Single-Molecule Nanocars". Nano Lett. 5 (11): 2330–34. Bibcode:2005NanoL...5.2330S. doi:10.1021/nl051915k. PMID 16277478.