• <tr id="yyy80"></tr>
  • <sup id="yyy80"></sup>
  • <tfoot id="yyy80"><noscript id="yyy80"></noscript></tfoot>
  • 99热精品在线国产_美女午夜性视频免费_国产精品国产高清国产av_av欧美777_自拍偷自拍亚洲精品老妇_亚洲熟女精品中文字幕_www日本黄色视频网_国产精品野战在线观看 ?

    基于全氟酞菁銅和碗烯雙分子體系在銀和石墨表面自組裝行為的低溫掃描隧道顯微鏡研究

    2017-05-10 17:42:42郭瑞張嘉霖趙宋燾余小江鐘舒孫碩李震宇陳偉
    物理化學(xué)學(xué)報(bào) 2017年3期
    關(guān)鍵詞:酞菁新加坡國立大學(xué)全氟

    郭瑞 張嘉霖, 趙宋燾 余小江 鐘舒 孫碩 李震宇 陳偉,,5,6,*

    (1新加坡國立大學(xué)化學(xué)系,新加坡117543;2新加坡國立大學(xué)物理系,新加坡117542;3中國科學(xué)技術(shù)大學(xué),合肥微尺度物質(zhì)科學(xué)國家實(shí)驗(yàn)室,中國科學(xué)院量子信息與量子科技前沿卓越創(chuàng)新中心,合肥23026;4新加坡國立大學(xué),新加坡同步加速器光源中心,新加坡117603;5新加坡國立大學(xué),先進(jìn)二維材料石墨烯研究中心,新加坡117546;6新加坡國立大學(xué)蘇州研究院,江蘇蘇州215123)

    基于全氟酞菁銅和碗烯雙分子體系在銀和石墨表面自組裝行為的低溫掃描隧道顯微鏡研究

    郭瑞1張嘉霖1,2趙宋燾3余小江4鐘舒1孫碩2李震宇3陳偉1,2,5,6,*

    (1新加坡國立大學(xué)化學(xué)系,新加坡117543;2新加坡國立大學(xué)物理系,新加坡117542;3中國科學(xué)技術(shù)大學(xué),合肥微尺度物質(zhì)科學(xué)國家實(shí)驗(yàn)室,中國科學(xué)院量子信息與量子科技前沿卓越創(chuàng)新中心,合肥23026;4新加坡國立大學(xué),新加坡同步加速器光源中心,新加坡117603;5新加坡國立大學(xué),先進(jìn)二維材料石墨烯研究中心,新加坡117546;6新加坡國立大學(xué)蘇州研究院,江蘇蘇州215123)

    由于其獨(dú)特的分子構(gòu)型和電子結(jié)構(gòu),碗烯被認(rèn)為是組成有機(jī)分子電子器件的一種重要的結(jié)構(gòu)單元。在不同金屬表面上單一組分的碗烯或其衍生物進(jìn)行自組裝的行為,及其所形成自組裝薄膜的電子結(jié)構(gòu)已經(jīng)被廣泛研究。這里我們利用低溫掃描隧道顯微鏡(LT-STM),對全氟酞菁銅和碗烯兩種組分在高定向熱解石墨和銀(111)兩種不同襯底上的自組裝結(jié)構(gòu)進(jìn)行了報(bào)道。在石墨襯底上,全氟酞菁銅和碗烯分子間形成的氫鍵成為雙分子網(wǎng)絡(luò)結(jié)構(gòu)能夠形成的關(guān)鍵;同時(shí),由于這種分子間氫鍵的存在,碗烯分子大多采取“開口朝下”的空間構(gòu)型,以保證分子間氫鍵最大限度的形成。但在銀襯底上觀察到的碗烯分子則隨機(jī)采取“開口向上”或“開口向下”兩種構(gòu)型,并沒有一種優(yōu)勢構(gòu)型的存在。我們認(rèn)為此時(shí)銀(111)襯底和有機(jī)分子間強(qiáng)烈的相互作用限制了碗烯兩種構(gòu)型之間的翻轉(zhuǎn),使得碗烯分子一旦被吸附就只能保持其原本的構(gòu)型,從而導(dǎo)致了在結(jié)果上兩種構(gòu)型的隨機(jī)分布。

    分子自組裝;雙分子網(wǎng)絡(luò)結(jié)構(gòu);碗烯;低溫掃描隧道顯微鏡;分子間氫鍵

    1 Introduc tion

    Corannulene(COR)is a bow l-shaped molecule and can be regarded asa fragmentof fullerene,asshown in Fig.1a.Since its first successful synthesis in 19661,COR has attracted intensive attention due to several intriguing properties.W ith fivefold symmetry,COR provides a unique opportunity to study the symmetrymismatching betweenadsorbateand substrate,given the incom patibility betw een the fivefold rotational symmetry of moleculeand translationalorder of theunderneath crystal lattice2. The combination of non-planar shapeand aromaticitymakes COR an interesting system w ith unique geometry and electronic properties2c.Specificπ-πinteractionsbetween curved and planar structures give rise tofascinating photoelectric properties3. Buckybow ls also serve as ideal hosts toform the host-guest complexes in supramolecular chem istry4.COR has alw ays been regarded as a fragment of C60molecule for its symmetry and conformation.Butconsidering itshigh solubility inmost common solvents2c,COR can be a better choice than fullerenes as a prom ising candidate for acceptormaterials in organic optoelectronic devices2c.Itshould bementioned thatKuvychko etal.5have recently reported a COR derivative(w ith electron w ithdraw ing groups)that has a higher electron affinity and thus can be a strongerelectron acceptor than thewell-studied C60.

    Two-dimensional(2D)self-assembly of functional organic molecules into ordered arrays represents one of themost promising strategies tofabricate functionalmolecular nanostructures overmacroscopicareas6.Modification ofmetalsurfaceswith COR and its derivativeshasbeen studied for symmetrym ismatch between substrate and adsorbate2a,7,multi-component packing4,8, templated assembly8a,9,interface dipole formation10,aswell as2D phase transitions6c,11.The assembly behaviors of the single-componentmoleculeswith fivefold symmetry on surfaceareof fundamental interest12.The structureof self-assembled CORmonolayer on Cu(111)and Cu(110)has been reported.On Cu(111), each CORmolecule adsorbson either fcc orhcp threefold hollow sitewith itsbow lopening pointing up11b.Oneof the fivehexagonal ringsorients parallel to the surface planeand thereforea tiltbetween molecular bow l w ith respect to the surface exists.A temperature-controlled reversible phase transitionwasalso observed in this system.It isexplained that low tem perature constrains the vibration of COR molecules,thus leads to amore effective intermolecular attraction,and finally results in the transition to the phasewith higher packing density11b.On Cu(110),asimilarquasihexagonal lattice with slightly tilted COR moleculeswas observed2a.In addition tomonolayer,a bilayer bow l-in-bow l stacking structure of COR wasalso reported on Cu(111)at low temperature13.Each second-layermolecule locatesdirectly aboveone firstlayermolecule,leading to the formation ofabow l-in-bow ldimer.

    In contrast to the intensive studies on single component selfassembly of COR and its derivatives,investigation on multicomponentmolecular assembled system consisting of COR is rarely reported.Multicomponent 2D assemblies providemore functionality and tunability for themolecular nanostructures14. Calmettes etal.8areported binarymolecular networks comprising 2,3,9,10,16,17,23,24-octachlorozinc phthalocyanine(ZnPcCl8)and the COR derivative of 1,3,5,7,9-penta-tertbutylcorannulene (PTBC).In this case,themetastable phaseof ZnPcCl8can beused asa flexible template to realize the controllable insertion of PTBC molecule.By selecting different phases formed by ZnPcCl8,the final bimolecular 2D structure,w hich resembles the original packing of template,canbe regulated.Xiao etal.4reported aCORC60buckybow l-buckyballhost-guestcomplexesby depositing C60onto the ordered monolayer of COR on Cu(110).The concave structure of COR is optimal to realize a“face-to-face”contact w ith the convex surface of C60and their com plementary electron environmentsare favorable for binding.Via thermalactivation,a strongly bound COR-C60host-guest system is formed.Delicate balance betw een various intermolecular and interfacial interactions plays essential role in tailoring these supramolecular structures6b,8a,14a,15.

    Herein we report the formation of self-assembled binarymolecular networks of COR and copper hexadecafluorophthalocyanine(F16CuPc)on the highly oriented pyrolytic graphite(HOPG) and Ag(111).Thegeometrical arrangementsof the binary system on differentsubstrateswere systematically investigated by lowtemperature scanning tunneling m icroscopy/spectroscopy(LT-STM/STS).

    2 Experim en talm ethods

    TheAg(111)and HOPG single crystalsubstratesare purchased from MaTeck Material-Technologie&Kristalle GmbH.The F16CuPc molecules are tw ice sublimed and purchased from CREAPHYS.Both sample preparation and investigation were performed in an ultrahigh vacuum system at a base pressure around 10-10mbar(1mbar=101Pa).TheAg(111)surfacewas prepared via repeated cycles of sputtering by Ar+and then annealing to 750K.Freshly cleaved HOPGwas thoroughly degassed in UHV at800 K overnight.COR and F16CuPc were thermally evaporated from separate Knudsen cells at 380 and 670 K,respectively,onto the substrate(keptatroom temperature).

    In-situ STM investigation was carried out in a custom-designed Om icron LT-STM w ith an electrochem ically etched tungsten tip scanning at77K.All STM imageswere obtained under constant currentmodewith biasvoltagesapplied to the tip.To collect the differential conductance d I/d V(local density of states),a lock-in techniquewasadopted togetherwith amodulation voltageof 50 m V and a frequency of 625 Hz.When ram ping the voltage,the feedback loopwasopened16.

    3 Resu lts and discussion

    F16CuPc,asshown in Fig.1bwas firstdeposited onto HOPG toform a self-assembledmonolayer.STM image(Fig.1c)clearly revealsa typical close packing structurewhere F16CuPcmolecules lie flat on substrate with theirmolecular planes parallel to the substrate,arising from the interfacialπ-πinteraction17.A unitcell w ith a=1.66 nm,b=3.5 nm,θ1=108°isoutlined in Fig.1c and schematic packingmodelof oneunitcell is shown in Fig.1d.Two differentmolecular orientations exist in F16CuPcmonolayer on HOPG,which hasbeen concretely analyzed in previous report17. In oneunit cell,theorientation of four F16CuPcmoleculeson the corner is deviated from thatof two F16CuPcmolecules centered at the b edge.Then COR molecules were evaporated onto the F16CuPc covered HOPG.Co-assembly of F16CuPc and COR,as shown in Fig.1eand 1f,formsa long range-ordered structurewith an intermixing ratio of 1:2.A unitcellwith c=2.87 nm,d=2.17 nm,θ2=114°is highlighted in Fig.1f and the schematic packing modelof one unit cell is shown in Fig.1g.It isnoteworthy that in the supramolecular structure,only one orientation of F16CuPc molecule isobserved and each F16CuPcmolecule issurrounded by 6CORmolecules.

    Fig.1 M olecu lar structures for(a)COR and(b)F16CuPc;(c)STM imageof F16CuPcmonolayer deposited on HOPG;(d)schematic packing structure for F16CuPcm oleculeon HOPG;(e,f)STM images of long range-ordered binarym olecular networks form ed by F16CuPc and CORw ith amolecular ratio of 1:2 on HOPG;(g)schematic packingmodel for the F16CuPc-COR binary structureon HOPGIn figure c:Theunitcell ishighlightedwith a=1.66 nm,b=3.5 nm,θ1=108°.Vtip=1.654V,20 nm×20 nm.In figurese,f:TheCORmoleculesadopting thebow lup and bow ldown configurationsare indicated by thearrows.Theunitcellishighlighted in the imagewith c=2.87 nm,d=2.17 nm,θ2=114°.Vtip=1.496V,20nm×20 nm;Vtip=1.496V,10 nm×10 nm

    Herewe observe two kinds of dotsaround F16CuPc,including the dots thatarebrighterand the dots thatare slightly darker.We propose both kinds of dots are CORmoleculesbutw ith different configurations:bow lopening pointing up and pointing down.STS measurements(Fig.2b)confirm this assumption and reveals the highest occupied molecular orbital(HOMO)-the lowest unoccupiedmolecular orbital(LUMO)gap of around 3.10 eV,which agreesw ith the theoretically calculated HOMO-LUMO gap of CORmolecule18.The simulated topographic STM imagesof COR,based on semiempiricalextended H?ckel calculation,have been used to determine the configuration of adsorbed COR by Parschau etal.2a.For bow lup configuration,both the HOMO and LUMO topographic simulated images show a density m inimum at the centerof themolecule togetherwith a distinct fivefold doughnut shape.On the contrary,for bow l down configuration,both the HOMO and LUMO topographic simulated imagesshow a density maximum at the centerof themolecule and theoutline of COR molecule is rather vague2a.Hence by com paring the simulated STM imagewith our high resolution STM results in Fig.2a,we assign these brighter dots to COR with bow lopening down and darkerdots to CORwith bow lopening up.

    Fig.2(a)High resolution STM image of the F16CuPc-COR binarymolecu lar networkson HOPG; (b)d I/d V spectra recorded on the bow l-up and bow l-down COR molecules

    It is noticed that in the F16CuPc-COR binary molecular networks on HOPG,COR molecules that adopt bow l-down configuration hold majority.We propose that this configuration preferencemay arise from the formation ofmultiple intermolecular hydrogen bonding.As F16CuPcmolecules lie flat on the plane, peripheral hydrogen atoms of CORmolecule w ith bow l-down configuration can stand closer to the neighboring F16CuPc,which facilitates the formation of multiple intermolecular hydrogen bonding between neighboring F16CuPc and COR.In thisway,the binary supramolecular structure iseffectively stabilized and bow ldown configuration of COR thus isenergetically favorable.

    Wealsogrew the same F16CuPc-COR binary system on Ag(111) to compare the co-assembly structureson differentsubstrates.Ag (111)has shownmuch strongermolecule-substrate interactions for variousorganic adsorbates19,compared w ith HOPG.Hencewe were able to grow amonolayer of COR onto Ag(111).A large scaleand thecorresponding closeup STM imagesof COR on Ag (111)are shown in Fig.3(a,b)with aunitcelloutlined(e=1.02 nm,f=1.17 nm,θ3=73°).Each CORmolecule isshared by four unit cells(Fig.3c).Likew ise,w e observe brighter and slightly darker dots in the STM image of COR monolayer.Careful inspection of high-resolution STM(Fig.3d)confirms the co-existenceof CORmoleculeswith differentconfigurations.Herein the brighter dot obviously has an intensity minimum in the center. Hence by using the aforementioned comparison of high-resolution STM imageswith simulated results,these brighter dots should be assigned to CORmoleculeswith bow ls opening up and the darker and vague dots should be COR moleculesw ith bow ls opening down.

    Fig.3(a)Large scale STM imageofCORmonolayer deposited on Ag(111);(b)closeup STM image of COR on Ag(111); (c)proposed schem atic packingm odel for COR on Ag(111);(d)high resolution STM im ageof COR on Ag(111)w ith the bow l-up and bow l-down configurations indicated by red arrowsIn figurea:Vtip=1.0V;60 nm×60 nm.In figureb:Theunitcellishighlighted by the red rhombusw ith e=1.02 nm,f=1.17 nm,θ3=73°; Vtip=1.0V,10 nm×10 nm.In figured:Vtip=-1.5V;6nm×6 nm

    Tofurther confirm our assignment,a comparison of the brighter dotson HOPG and Ag(111)underhigh-resolution STM is shown in Fig.4.It isobvious thatin Fig.4a,the CORmoleculewithbow lup configuration possesses a hollow center w ith a rough pentagonal doughnutshape,which is consistentwith features of thesimulated bow l-up COR.While in Fig.4b,the COR molecule accounted asbow l-dow n configuration ismore protruding in the center and themolecule shape is obscure,which also resembles simulated bow l-down topography.We noted that on Ag(111) substrate,the configuration preference of COR disappears:both bow l-up and bow l-down COR exist in almostequalamount.In otherwords,the adoption of bow l-up or bow l-down configuration is random.We suggest that the strong COR-Ag(111)interfacial interaction constrains themovementand bow l inversion of COR molecules.Onceadsorbed on Ag(111),CORmolecule could only retain its initial configuration and therefore both configurations have equal chance to appear.

    Fig.4 Com parison of the brighter dotsunder high-resolution STM(a)CORmoleculew ith bow l-up configurationon Ag(111); (b)CORmoleculewith bow l-down configuration on HOPG

    Fig.5(a)High resolution STM imageof F16CuPc-COR binary m olecular networks on Ag(111)w ith am olecular ratio of 1:4; (b)schem atic pack ingm odel for the F16CuPc-COR b inary structureon Ag(111)In figurea:Theunitcellishighlighted by the red rhombusw ith g=h=2.73 nm,θ4=100°.Vtip=1.26V,10 nm×10 nm

    Co-assemblymonolayerof F16CuPc and COR on Ag(111)was also prepared by furtherevaporating F16CuPcmolecules onto the COR covered substrate.STM image reveals the long range-ordered binarymolecularnetworksw ith amolecular ratio of 1:4. The unit cell isoutlined in Fig.5aw ith features including g=h= 2.73 nm andθ4=100°.Corresponding schematic packingmodel for the binary structure is shown in Fig.5b.All the F16CuPc molecules lie in the same orientation and each F16CuPcmolecule issurrounded by 8CORmolecules.

    4 Conc lusions

    In summary,we have investigated the binary supramolecular structureof F16CuPc-CORmonolayerassembled on HOPGand Ag (111)substrates.The formation of multiple intermolecular hydrogen bonding between F16CuPc and COR could result in a preferred bow l-dow n configuration for COR molecules on the weakly interacting HOPG.In contrast,this configuration preference disappears on Ag(111)substrate where the adoption of bow l-up orbow l-down configuration is random,resulting from the strongmolecule-substrate interactions.Ourwork would further reinforce themodification of surfacew ith binarymolecular networks consisting ofCOR and itsderivatives.

    (1)Barth,W.E.;Law ton,R.G.J.Am.Chem.Soc.1966,88(2), 380.doi:10.1021/ja00954a049

    (2)(a)Parschau,M.;Fasel,R.;Ernst,K.H.;Gr?ning,O.; B randenberger,L.;Schillinger,R.;Greber,T.;Seitsonen,A.P.; Wu,Y.T.;Siegel,J.S.Angew.Chem.-Int.Edit.2007,46(43), 8258.doi:10.1002/anie.200700610

    (b)Shechtman,D.;Blech,I.;Gratias,D.;Cahn,J.W.Phys.Rev. Lett.1984,53(20),1951.doi:10.1103/PhysRevLett.53.1951

    (c)Bauert,E.FundamentalAspectsof the Self-assembly Behaviorand Electronic Propertiesof Corannulenes.Ph.D. Dissertation,University of Zurich,Zurich,2011.

    (3)Li,J.;Liu,Y.;Qian,Y.;Li,L.;Xie,L.;Shang,J.;Yu,T.;Yi,M.; Huang,W.Phys.Chem.Chem.Phys.2013,15(30),12694. doi:10.1039/C3CP51095F

    (4)Xiao,W.;Passerone,D.;Ruffieux,P.;A?t-M ansour,K.; G r?ning,O.;Tosatti,E.;Siegel,J.S.;Fasel,R.J.Am.Chem. Soc.2008,130(14),4767.doi:10.1021/ja077816l

    (5)Kuvychko,I.V.;Dubceac,C.;Deng,S.H.;Wang,X.B.; G ranovsky,A.A.;Popov,A.A.;Petrukhina,M.A.;Strauss,S. H.;Boltalina,O.V.Angew.Chem.-Int.Edit.2013,52(29), 7505.doi:10.1002/anie.201300796

    (6)(a)Baris,B.;Jeannoutot,J.;Luzet,V.;Palmino,F.;Rochefort, A.;Cherioux,F.ACSNano 2012,6(8),6905.doi:10.1021/ nn301827e

    (b)Mali,K.S.;De Feyter,S.Phil.Trans.R.Soc.A 2013,371 (2000),20120304.doi:10.1098/rsta.2012.0304

    (c)Zoppi,L.;Bauert,T.;Siegel,J.S.;Baldridge,K.K.;Ernst, K.H.Phys.Chem.Chem.Phys.2012,14(38),13365. doi:10.1039/C2CP41732D

    (7)Guillermet,O.;Niem i,E.;Nagarajan,S.;Bouju,X.;Martrou, D.;Gourdon,A.;Gauthier,S.Angew.Chem.-Int.Edit.2009,48 (11),1970.doi:10.1002/anie.200805689

    (8)(a)Calmettes,B.;Nagarajan,S.;Gourdon,A.;Abel,M.;Porte, L.;Coratger,R.Angew.Chem.-Int.Edit.2008,47(37),6994. doi:10.1002/anie.200802628

    (b)Yokoi,H.;Hiraoka,Y.;Hiroto,S.;Sakamaki,D.;Seki,S.; Shinokubo,H.Nat.Commun.2015,6.doi:10.1038/

    ncomms9215

    (9)Balandina,T.;Tahara,K.;Sandig,N.;Blunt,M.O.;Adisoejoso, J.;Lei,S.;Zerbetto,F.;Tobe,Y.;De Feyter,S.ACSNano 2012, 6(9),8381.doi:10.1021/nn303144r

    (10)Bauert,T.;Zoppi,L.;Koller,G.;Garcia,A.;Baldridge,K.K.; Ernst,K.H.J.Phys.Chem.Lett.2011,2(21),2805. doi:10.1021/jz2012484

    (11)(a)M erz,L.;Bauert,T.;Parschau,M.;Koller,G.;Siegel,J.S.; Ernst,K.H.Chem.Commun.2009,(39),5871.doi:10.1039/ B911056A (b)M erz,L.;Parschau,M.;Zoppi,L.;Baldridge,K.K.;Siegel, J.S.;Ernst,K.H.Angew.Chem.-Int.Edit.2009,48(11),1966. doi:10.1002/anie.200804563

    (12)(a)Bauert,T.;Merz,L.;Bandera,D.;Parschau,M.;Siegel,J.S.; Ernst,K.H.J.Am.Chem.Soc.2009,131(10),3460. doi:10.1021/ja8101083. (b)Merz,L.;Parschau,M.;Siegel,J.S.;Ernst,K.H.Chimia 2009,63(4),214.doi:10.2533/chim ia.2009.214

    (13)Bauert,T.;Baldridge,K.K.;Siegel,J.S.;Ernst,K.H.Chem. Commun.2011,47(28),7995.doi:10.1039/C1CC12540K.

    (14)(a)De Oteyza,D.G.MulticomponentAssembly Strategies for Supramolecular Systems.In SupramolecularMaterialsforOpto-Electronics;Nobert Korch;Royal Society of Chem istry: Cambridge,2014;pp 53-97.doi:10.1039/9781782626947-00053 (b)Huang,Y.L.;Chen,W.;Li,H.;Ma,J.;Pflaum,J.;Wee,A.T. S.Small2010,6(1),70.doi:10.1002/sm ll.200901291

    (15)Zhong,J.Q.;Qin,X.;Zhang,J.L.;Kera,S.;Ueno,N.;Wee,A. T.S.;Yang,J.;Chen,W.ACSNano 2014,8(2),1699. doi:10.1021/nn406050e

    (16)Zhang,J.;Wang,Z.;Niu,T.;Li,Z.;Chen,W.Appl.Phys.Lett. 2014,104(11),113506.doi:10.1063/1.4869115

    (17)Huang,Y.L.;Chen,W.;Chen,S.;Wee,A.T.S.Appl.Phys.A 2009,95(1),107.doi:10.1007/s00339-008-5000-6

    (18)dos Santos,R.B.;Rivelino,R.;de M ota,F.B.;Gueorguiev,G. K.J.Phys.Chem.A 2012,116(36),9080.doi:10.1021/ jp3049636

    (19)(a)Lackinger,M.;Griessl,S.;Heckl,W.M.;Hietschold,M. J.Phys.Chem.B 2002,106(17),4482.doi:10.1021/jp014275s (b)Lackinger,M.;Hietschold,M.Surf.Sci.2002,520(1), L619.doi:10.1016/S0039-6028(02)02269-0

    LT-STM Investigation of the Self-Assem bled F16CuPc-Co rannu lene Binary System on Ag(111)and Graphite Surfaces

    GUO Rui1ZHANG Jialin1,2ZHAO Songtao3YU Xiaojiang4ZHONG Shu1SUN Shuo2LIZhenyu3CHENWei1,2,5,6,*
    (1DepartmentofChemistry,NationalUniversity ofSingapore,3Science Drive 3,117543,Singapore;2DepartmentofPhysics,NationalUniversity ofSingapore,2Science Drive 3,117542,Singapore;3HefeiNational Laboratory for PhysicalSciencesat the Microscale,CASCentre for Excellence and Synergetic Innovation Center of Quantum Information and Quantum Physics,University ofScience and Technology ofChina,Hefei230026,P.R.China;
    4Singapore Synchrotron LightSource,National University ofSingapore,5 Research Link,117603,Singapore;
    5Centerfor Advanced 2DMaterialsand Graphene Research Center,NationalUniversity ofSingapore,3 Science Drive 3,117546,
    Singapore;6NationalUniversity ofSingapore(Suzhou)Research Institute,Suzhou 215123,Jiangsu Province,P.R.China)

    Mo lecularassembly;Binarymolecularnetworks;Corannulene;Low-temperature scanning tunne lingm icroscopy;Intermo lecularhyd rogen bonding

    O647

    10.3866/PKU.WHXB201612051

    www.whxb.pku.edu.cn

    Received:September 29,2016;Revised:December 2,2016;Published online:December 5,2016.

    *Corresponding author.Email:phycw@nus.edu.sg;Tel:+65-65161879.

    Theprojectwas supported by theNational Key Basic Research Program of China(973)(2015CB856505),SingaporeMOE(R143-000-652-112),

    Singapore NRF-CRPgrantof“Doped Contacts and Heterostructures for Solution-Processable Plastic Electronics”(R143-001-608-281),Jiangsu

    Province GovernmentResearch Platform Grant,China,and NUSRISeed Fund.

    國家重點(diǎn)基礎(chǔ)研究發(fā)展規(guī)劃項(xiàng)目(973)(2015CB856505),新加坡教育部(MOE,Tier II,R143-000-652-112),新加坡國家研發(fā)基金會(NRF,R143-001-608-281),江蘇省平臺建設(shè)項(xiàng)目和新加坡國立大學(xué)蘇州研究院資助?Editorialoffice of Acta Physico-Chim ica Sinica

    Abstract:Corannulene(COR)is considered a prom isingmolecularbuilding block fororganic electronics owing to its intriguing geome trical and e lec tronic p roperties.Intensive research e fforts have been devoted to understanding the assemb ly behavior and e lectronic structure of COR and its derivatives on variousmeta l surfaces via low-temperature scanning tunne lingm icroscopy(LT-STM).Here we report the formation ofbinary mo lecular networks of copperhexadeca fluorophtha locyanine(F16CuPc)-COR self-assembled on the highly oriented pyrolytic graphite(HOPG)and Ag(111)substrates.Intermo lecularhydrogen bonding between F16CuPc and COR facilitates the formation ofbina rymolecular networks on HOPG and further induces a pre ference for bow l-down configured CORmolecules.This observed configuration preference disappears on Ag(111)substrate, where CORmolecules lie on the substrate with theirbow lopenings pointing up and down random ly.We propose tha tstrong interfacia l interactions betw een them olecule and Ag(111)su rface constrain the bow l inve rsion of the CORmo lecule,which thus retains its initialconfiguration upon adsorption.

    猜你喜歡
    酞菁新加坡國立大學(xué)全氟
    全氟烷基化合物暴露與成年人抑郁癥間的關(guān)系:基于NHANES 2005~2018
    新加坡國立大學(xué)推出新型止血敷料
    新加坡國立大學(xué)助力重慶企業(yè)研發(fā)區(qū)塊鏈技術(shù)
    追光花園
    2-硝基酞菁鋁的合成及其催化活性研究
    安徽化工(2018年4期)2018-09-03 07:11:48
    新加坡國立大學(xué)卓越辦學(xué)經(jīng)驗(yàn)及啟示
    大學(xué)(2016年4期)2016-04-09 06:39:22
    1種制備全氟聚醚羧酸的方法
    1種制備全氟烯醚磺酰氟化合物的方法
    纖維素纖維負(fù)載鈷酞菁對活性染料X-3B的降解
    四羧基酞菁鋅鍵合MCM=41的合成及其對Li/SOCl2電池催化活性的影響
    日本一二三区视频观看| 日韩av在线大香蕉| 在线永久观看黄色视频| 国产午夜福利久久久久久| 日本熟妇午夜| netflix在线观看网站| 91大片在线观看| 国产精品美女特级片免费视频播放器 | 搞女人的毛片| 九色国产91popny在线| 久久精品国产99精品国产亚洲性色| 久9热在线精品视频| 亚洲九九香蕉| 国产精品精品国产色婷婷| 免费电影在线观看免费观看| 无遮挡黄片免费观看| 国产高清视频在线播放一区| 岛国在线观看网站| 亚洲欧美日韩高清在线视频| 啪啪无遮挡十八禁网站| 国产一区二区在线观看日韩 | 一进一出好大好爽视频| 国产一区在线观看成人免费| 亚洲国产精品sss在线观看| 亚洲全国av大片| 麻豆久久精品国产亚洲av| 欧美日韩瑟瑟在线播放| 日韩精品中文字幕看吧| 日韩欧美在线乱码| 99精品在免费线老司机午夜| 成人18禁在线播放| 蜜桃久久精品国产亚洲av| 久久精品国产99精品国产亚洲性色| 亚洲一区高清亚洲精品| 国产成人欧美在线观看| 亚洲一区高清亚洲精品| 午夜激情福利司机影院| 欧美色欧美亚洲另类二区| 在线观看日韩欧美| 日韩高清综合在线| 久久久久国内视频| 亚洲黑人精品在线| 亚洲七黄色美女视频| 欧美日韩乱码在线| 在线观看美女被高潮喷水网站 | 午夜a级毛片| 啦啦啦免费观看视频1| 日韩成人在线观看一区二区三区| 男女午夜视频在线观看| 在线视频色国产色| 国产男靠女视频免费网站| 国产野战对白在线观看| 精华霜和精华液先用哪个| av中文乱码字幕在线| 午夜影院日韩av| 村上凉子中文字幕在线| 亚洲美女黄片视频| 免费看a级黄色片| 亚洲 国产 在线| 亚洲专区中文字幕在线| 神马国产精品三级电影在线观看 | 欧美成狂野欧美在线观看| 禁无遮挡网站| 日韩高清综合在线| av超薄肉色丝袜交足视频| 麻豆av在线久日| 黄片大片在线免费观看| 国产精品 国内视频| 亚洲av熟女| 欧美性猛交╳xxx乱大交人| 精品国产乱码久久久久久男人| 日韩大码丰满熟妇| 一级片免费观看大全| 又大又爽又粗| 高清毛片免费观看视频网站| www.www免费av| 岛国在线免费视频观看| 欧美zozozo另类| 最近最新中文字幕大全免费视频| а√天堂www在线а√下载| 亚洲精品中文字幕一二三四区| 嫁个100分男人电影在线观看| 久久香蕉激情| 亚洲成人久久爱视频| 国产精品美女特级片免费视频播放器 | 一区福利在线观看| 免费电影在线观看免费观看| 亚洲,欧美精品.| 天堂动漫精品| 叶爱在线成人免费视频播放| 色播亚洲综合网| 91国产中文字幕| 1024手机看黄色片| 美女 人体艺术 gogo| 狂野欧美白嫩少妇大欣赏| 97超级碰碰碰精品色视频在线观看| 狂野欧美激情性xxxx| 精品久久久久久久久久久久久| 日日爽夜夜爽网站| 欧美zozozo另类| 老汉色av国产亚洲站长工具| 亚洲av美国av| 久久久水蜜桃国产精品网| 亚洲精品美女久久av网站| 久久久久久久午夜电影| 久久久久久大精品| 床上黄色一级片| 亚洲性夜色夜夜综合| 国产精品av久久久久免费| 男女视频在线观看网站免费 | 国内精品一区二区在线观看| 中文亚洲av片在线观看爽| 此物有八面人人有两片| 五月伊人婷婷丁香| 久久精品aⅴ一区二区三区四区| 十八禁网站免费在线| 中文字幕熟女人妻在线| 69av精品久久久久久| 操出白浆在线播放| 精品久久久久久成人av| 91老司机精品| 看黄色毛片网站| 日本熟妇午夜| 999久久久精品免费观看国产| 日韩欧美国产一区二区入口| 色在线成人网| 少妇被粗大的猛进出69影院| 深夜精品福利| 嫩草影院精品99| 母亲3免费完整高清在线观看| 麻豆av在线久日| 成人av在线播放网站| 欧美一级毛片孕妇| 久久国产精品人妻蜜桃| 国产伦在线观看视频一区| 又黄又粗又硬又大视频| 日韩中文字幕欧美一区二区| 波多野结衣高清无吗| 国产av在哪里看| 国产精品一及| 国产亚洲欧美在线一区二区| 免费观看人在逋| 亚洲aⅴ乱码一区二区在线播放 | 岛国在线观看网站| 动漫黄色视频在线观看| 午夜免费成人在线视频| 国产免费av片在线观看野外av| 国产欧美日韩精品亚洲av| 日本免费a在线| 午夜福利在线观看吧| 久久久精品国产亚洲av高清涩受| 又爽又黄无遮挡网站| 亚洲欧洲精品一区二区精品久久久| 午夜日韩欧美国产| 亚洲精品一卡2卡三卡4卡5卡| 欧美又色又爽又黄视频| 日韩 欧美 亚洲 中文字幕| 国产91精品成人一区二区三区| 俄罗斯特黄特色一大片| 母亲3免费完整高清在线观看| 麻豆成人午夜福利视频| 女人被狂操c到高潮| 亚洲天堂国产精品一区在线| 免费观看精品视频网站| 超碰成人久久| 不卡一级毛片| 99re在线观看精品视频| 亚洲精品美女久久久久99蜜臀| 日韩欧美免费精品| 一本久久中文字幕| 欧美一级毛片孕妇| 黄色a级毛片大全视频| 99久久99久久久精品蜜桃| 国产精品1区2区在线观看.| 女人高潮潮喷娇喘18禁视频| 国产av一区二区精品久久| or卡值多少钱| 母亲3免费完整高清在线观看| 99热6这里只有精品| 欧美成人免费av一区二区三区| 一级毛片女人18水好多| 精品少妇一区二区三区视频日本电影| 午夜视频精品福利| 欧美又色又爽又黄视频| 老汉色av国产亚洲站长工具| 亚洲精品中文字幕一二三四区| 99精品久久久久人妻精品| 丰满人妻熟妇乱又伦精品不卡| 欧美日本视频| 999久久久精品免费观看国产| 2021天堂中文幕一二区在线观| 亚洲,欧美精品.| av视频在线观看入口| 久久久国产成人免费| 欧美一级毛片孕妇| 日韩欧美在线乱码| 免费在线观看影片大全网站| 18禁黄网站禁片免费观看直播| 19禁男女啪啪无遮挡网站| 国产精品久久久久久人妻精品电影| 国产熟女午夜一区二区三区| 国产成人啪精品午夜网站| 亚洲国产欧美网| 国产精品99久久99久久久不卡| 无遮挡黄片免费观看| 久久香蕉国产精品| 最近最新免费中文字幕在线| 亚洲一区高清亚洲精品| 九色国产91popny在线| 国内精品一区二区在线观看| 一区二区三区激情视频| 成人一区二区视频在线观看| 欧美性长视频在线观看| 久久久久亚洲av毛片大全| 久久99热这里只有精品18| a级毛片a级免费在线| 亚洲精华国产精华精| 久久久精品国产亚洲av高清涩受| 99热这里只有是精品50| 欧美激情久久久久久爽电影| 国产精品综合久久久久久久免费| 一a级毛片在线观看| 中文字幕熟女人妻在线| 国产欧美日韩一区二区精品| 蜜桃久久精品国产亚洲av| 香蕉久久夜色| 日本黄大片高清| av国产免费在线观看| 波多野结衣高清无吗| 精品国产美女av久久久久小说| 亚洲自拍偷在线| 免费在线观看完整版高清| 最近最新中文字幕大全免费视频| 久久香蕉激情| 成熟少妇高潮喷水视频| 亚洲av片天天在线观看| 国产亚洲精品久久久久久毛片| 久久精品人妻少妇| 久久亚洲精品不卡| 国产精品九九99| 亚洲国产精品成人综合色| 可以在线观看的亚洲视频| 成人18禁在线播放| 一本综合久久免费| 三级国产精品欧美在线观看 | 欧美一区二区精品小视频在线| 欧美在线黄色| 久久香蕉国产精品| 欧美黑人巨大hd| 国产亚洲欧美98| 可以在线观看毛片的网站| 白带黄色成豆腐渣| 女人高潮潮喷娇喘18禁视频| 国产精品免费一区二区三区在线| 欧美zozozo另类| 狂野欧美激情性xxxx| 人人妻人人看人人澡| av福利片在线观看| 天天躁狠狠躁夜夜躁狠狠躁| 国产精品免费一区二区三区在线| 亚洲七黄色美女视频| 亚洲成a人片在线一区二区| 国内精品久久久久精免费| 少妇熟女aⅴ在线视频| av中文乱码字幕在线| 亚洲国产欧美人成| 欧美成狂野欧美在线观看| 精品久久蜜臀av无| 亚洲欧美日韩高清在线视频| av福利片在线观看| 美女午夜性视频免费| 国产精品精品国产色婷婷| 午夜福利视频1000在线观看| 久久精品国产99精品国产亚洲性色| 日日夜夜操网爽| 亚洲中文字幕日韩| 18禁国产床啪视频网站| 国产精品久久视频播放| 亚洲avbb在线观看| 一本综合久久免费| 97碰自拍视频| 亚洲av美国av| a级毛片在线看网站| 久久久国产成人精品二区| 久久精品国产综合久久久| 国产亚洲精品久久久久久毛片| www日本黄色视频网| 91av网站免费观看| 两人在一起打扑克的视频| 日日爽夜夜爽网站| 午夜视频精品福利| 久久精品影院6| 亚洲成av人片免费观看| 蜜桃久久精品国产亚洲av| 日韩国内少妇激情av| 午夜影院日韩av| 日韩欧美免费精品| 欧美3d第一页| 欧美日本视频| 国产三级中文精品| 久久香蕉国产精品| 真人一进一出gif抽搐免费| 欧美大码av| 日本成人三级电影网站| 欧美日本亚洲视频在线播放| 国产亚洲欧美在线一区二区| 别揉我奶头~嗯~啊~动态视频| 国产人伦9x9x在线观看| 亚洲av五月六月丁香网| 国产一区在线观看成人免费| 露出奶头的视频| 国产熟女午夜一区二区三区| 精品第一国产精品| 一二三四在线观看免费中文在| 五月伊人婷婷丁香| 久久人妻福利社区极品人妻图片| 三级毛片av免费| 亚洲欧美日韩高清在线视频| 亚洲精品中文字幕在线视频| 五月玫瑰六月丁香| 免费搜索国产男女视频| 国产高清videossex| 国产亚洲av高清不卡| 久久中文看片网| 男插女下体视频免费在线播放| 国产av一区在线观看免费| 亚洲精品一卡2卡三卡4卡5卡| 日韩成人在线观看一区二区三区| 国产一区二区三区在线臀色熟女| 欧美色视频一区免费| 亚洲在线自拍视频| 成人特级黄色片久久久久久久| 在线观看一区二区三区| 美女 人体艺术 gogo| 一卡2卡三卡四卡精品乱码亚洲| 在线十欧美十亚洲十日本专区| 亚洲真实伦在线观看| 丝袜美腿诱惑在线| 国产成人欧美在线观看| 又黄又粗又硬又大视频| 国产亚洲精品第一综合不卡| 露出奶头的视频| 欧美日韩一级在线毛片| 免费一级毛片在线播放高清视频| 我的老师免费观看完整版| 天堂动漫精品| 成人手机av| 法律面前人人平等表现在哪些方面| 老司机在亚洲福利影院| 国产精品香港三级国产av潘金莲| 搡老妇女老女人老熟妇| 最新在线观看一区二区三区| www日本在线高清视频| 欧美黑人精品巨大| 国产精品久久视频播放| 欧美久久黑人一区二区| 午夜视频精品福利| 亚洲人成77777在线视频| 最新在线观看一区二区三区| 欧美乱码精品一区二区三区| 美女免费视频网站| 51午夜福利影视在线观看| 中出人妻视频一区二区| 超碰成人久久| 男女做爰动态图高潮gif福利片| 免费看十八禁软件| 高潮久久久久久久久久久不卡| 欧美日韩黄片免| 男女床上黄色一级片免费看| tocl精华| 真人做人爱边吃奶动态| 国产爱豆传媒在线观看 | 亚洲国产中文字幕在线视频| 久热爱精品视频在线9| 黄片小视频在线播放| 最近在线观看免费完整版| 国产1区2区3区精品| 两个人的视频大全免费| 视频区欧美日本亚洲| 亚洲免费av在线视频| 在线十欧美十亚洲十日本专区| 国产主播在线观看一区二区| 黄片大片在线免费观看| 欧美一级a爱片免费观看看 | 久久天躁狠狠躁夜夜2o2o| 亚洲第一电影网av| 亚洲人成网站在线播放欧美日韩| 中文字幕人妻丝袜一区二区| 欧美日韩一级在线毛片| 久久精品国产综合久久久| 国产精品香港三级国产av潘金莲| 一本一本综合久久| 日日爽夜夜爽网站| 嫩草影视91久久| 国产成人精品久久二区二区91| 国产精品 欧美亚洲| 每晚都被弄得嗷嗷叫到高潮| a级毛片a级免费在线| 亚洲成a人片在线一区二区| 久久久久免费精品人妻一区二区| 亚洲国产精品999在线| 免费人成视频x8x8入口观看| 日韩欧美国产在线观看| 欧美日韩黄片免| 亚洲无线在线观看| 日韩有码中文字幕| 国产伦一二天堂av在线观看| 久久精品夜夜夜夜夜久久蜜豆 | 蜜桃久久精品国产亚洲av| 日本黄大片高清| 中文字幕熟女人妻在线| 国产精品久久电影中文字幕| 久热爱精品视频在线9| 日韩欧美三级三区| 亚洲人与动物交配视频| 老司机深夜福利视频在线观看| 亚洲片人在线观看| 给我免费播放毛片高清在线观看| 亚洲 欧美一区二区三区| 国产精品久久久久久亚洲av鲁大| 99国产精品一区二区蜜桃av| 99热这里只有是精品50| 亚洲自拍偷在线| 久久久久九九精品影院| 男男h啪啪无遮挡| 日韩欧美精品v在线| 免费搜索国产男女视频| 久久久精品大字幕| 国产三级中文精品| 日本a在线网址| 制服人妻中文乱码| 国产99白浆流出| 久久久国产精品麻豆| 人妻久久中文字幕网| 不卡一级毛片| 午夜亚洲福利在线播放| 中文字幕最新亚洲高清| 日本免费一区二区三区高清不卡| 18禁美女被吸乳视频| 人妻丰满熟妇av一区二区三区| 欧美+亚洲+日韩+国产| 两个人视频免费观看高清| 成人18禁高潮啪啪吃奶动态图| 久久久久久免费高清国产稀缺| 久久久国产精品麻豆| 婷婷丁香在线五月| 国产99白浆流出| 亚洲欧美一区二区三区黑人| 日本一本二区三区精品| 男女午夜视频在线观看| av超薄肉色丝袜交足视频| 99国产精品99久久久久| 国产主播在线观看一区二区| 一级作爱视频免费观看| 国产精品国产高清国产av| 国产av不卡久久| 欧美3d第一页| 亚洲 欧美 日韩 在线 免费| 90打野战视频偷拍视频| 国产精品 欧美亚洲| 很黄的视频免费| 熟妇人妻久久中文字幕3abv| 国产成年人精品一区二区| 久久久久久亚洲精品国产蜜桃av| 18美女黄网站色大片免费观看| 国产精品野战在线观看| 国产免费av片在线观看野外av| 99精品久久久久人妻精品| 老司机深夜福利视频在线观看| 99精品欧美一区二区三区四区| 欧美中文日本在线观看视频| 国产一级毛片七仙女欲春2| 精品免费久久久久久久清纯| 久久热在线av| 免费看a级黄色片| 午夜福利在线观看吧| 中文字幕高清在线视频| 草草在线视频免费看| 狂野欧美白嫩少妇大欣赏| 国产精品98久久久久久宅男小说| 久久久水蜜桃国产精品网| 精品欧美一区二区三区在线| 精品一区二区三区视频在线观看免费| 亚洲七黄色美女视频| 国产激情欧美一区二区| 18禁黄网站禁片免费观看直播| 后天国语完整版免费观看| 757午夜福利合集在线观看| 长腿黑丝高跟| √禁漫天堂资源中文www| av中文乱码字幕在线| 男人的好看免费观看在线视频 | 九色成人免费人妻av| 色av中文字幕| 日韩欧美 国产精品| 色精品久久人妻99蜜桃| 好看av亚洲va欧美ⅴa在| 亚洲av成人av| 亚洲av电影不卡..在线观看| 日韩免费av在线播放| 男女视频在线观看网站免费 | 男女床上黄色一级片免费看| 可以免费在线观看a视频的电影网站| 日韩中文字幕欧美一区二区| 精品免费久久久久久久清纯| 精品国产乱子伦一区二区三区| 国内揄拍国产精品人妻在线| 可以在线观看的亚洲视频| 一边摸一边做爽爽视频免费| 精品免费久久久久久久清纯| 日日夜夜操网爽| 丰满的人妻完整版| 精品无人区乱码1区二区| 日韩中文字幕欧美一区二区| 精品免费久久久久久久清纯| 成人精品一区二区免费| 国产成年人精品一区二区| √禁漫天堂资源中文www| 午夜影院日韩av| 午夜精品久久久久久毛片777| 精品少妇一区二区三区视频日本电影| 亚洲九九香蕉| 国产1区2区3区精品| 香蕉av资源在线| 精品久久久久久成人av| 女人高潮潮喷娇喘18禁视频| 日本一区二区免费在线视频| 国产视频一区二区在线看| 免费人成视频x8x8入口观看| 真人做人爱边吃奶动态| 1024香蕉在线观看| 91麻豆av在线| 亚洲精品在线观看二区| 在线观看免费午夜福利视频| 久久香蕉精品热| 一级片免费观看大全| 搞女人的毛片| videosex国产| 久久久精品大字幕| 国产精品香港三级国产av潘金莲| 最新在线观看一区二区三区| 欧美+亚洲+日韩+国产| 好男人在线观看高清免费视频| av福利片在线观看| 久久久久久久精品吃奶| 午夜日韩欧美国产| 99在线人妻在线中文字幕| xxx96com| 免费电影在线观看免费观看| 久久国产精品人妻蜜桃| 在线永久观看黄色视频| 日本三级黄在线观看| 国产又色又爽无遮挡免费看| 特大巨黑吊av在线直播| 久久久国产欧美日韩av| 很黄的视频免费| 亚洲专区中文字幕在线| 1024手机看黄色片| 黑人巨大精品欧美一区二区mp4| 99久久无色码亚洲精品果冻| 99国产精品一区二区三区| 久久久久久大精品| 一区二区三区国产精品乱码| 变态另类丝袜制服| 日本一本二区三区精品| 91麻豆精品激情在线观看国产| 亚洲avbb在线观看| 国产不卡一卡二| 法律面前人人平等表现在哪些方面| 一a级毛片在线观看| 午夜福利成人在线免费观看| 国产一区在线观看成人免费| 少妇的丰满在线观看| 久久人人精品亚洲av| 成年免费大片在线观看| 人人妻,人人澡人人爽秒播| 久久久国产成人免费| 妹子高潮喷水视频| 高清毛片免费观看视频网站| av免费在线观看网站| 国产精品久久久久久人妻精品电影| 国产伦一二天堂av在线观看| 叶爱在线成人免费视频播放| 国产成人精品久久二区二区免费| 久久香蕉国产精品| 国产精品电影一区二区三区| 亚洲,欧美精品.| 91大片在线观看| 精品国产美女av久久久久小说| 亚洲男人的天堂狠狠| 色噜噜av男人的天堂激情| 久久久国产成人精品二区| 亚洲欧美日韩无卡精品| 欧美丝袜亚洲另类 | 无人区码免费观看不卡| 日本免费一区二区三区高清不卡| 午夜福利视频1000在线观看| 国产视频一区二区在线看| 又大又爽又粗| 在线a可以看的网站| a级毛片在线看网站| 黄色成人免费大全| 99riav亚洲国产免费| 麻豆成人av在线观看| 在线观看午夜福利视频| 一二三四在线观看免费中文在| 欧美成人性av电影在线观看| 精品福利观看| a级毛片在线看网站| 变态另类成人亚洲欧美熟女| 色精品久久人妻99蜜桃| 午夜激情av网站| 免费看十八禁软件| 午夜两性在线视频| 久久久久九九精品影院|