Photo-regulation of 2D supramolecular self-assembly: On-surface photochemistry studied by STM
- Corresponding author: Zeng Qing-Dao, zengqd@nanoctr.cn Wang Chen, wangch@nanoctr.cn
Citation:
Dai Hong-Liang, Geng Yan-Fang, Zeng Qing-Dao, Wang Chen. Photo-regulation of 2D supramolecular self-assembly: On-surface photochemistry studied by STM[J]. Chinese Chemical Letters,
;2017, 28(4): 729-737.
doi:
10.1016/j.cclet.2016.09.018
Wang D., Chen Q., Wan L.J.. Structural transition of molecular assembly under photo-irradiation:an STM study[J]. Phys.Chem.Chem.Phys., 2008,10:6467-6478. doi: 10.1039/b810304f
Henzl J., Bredow T.. Morgenstern K.Irreversible isomerization of the azobenzene derivate methyl orange on Au(111)[J]. Chem.Phys.Lett., 2007,435:278-282. doi: 10.1016/j.cplett.2006.12.096
Martin M., Lastapis M., Riedel D.. Mastering the molecular dynamics of a bistable molecule by single atom manipulation[J]. Phys.Rev.Lett., 2006,97216103. doi: 10.1103/PhysRevLett.97.216103
Henzl J., Mehlhorn M., Gawronski H., Rieder K.H., Morgenstern K.. Reversible cis-trans isomerization of a single azobenzene molecule[J]. Angew.Chem.Int.Ed., 2006,45:603-606. doi: 10.1002/(ISSN)1521-3773
Spillmann H., Kiebele A., Stöhr M.. A two-dimensional porphyrin-based porous network featuring communicating cavities for the templated complexation of fullerenes[J]. Adv.Mater., 2006,18:275-279. doi: 10.1002/(ISSN)1521-4095
Griessl S., Lackinger M., Edelwirth M., Hietschold M., Heckl W.M.. Self-assembled two-dimensional molecular host-guest architectures from trimesic acid[J]. Single Mol., 2002,3:25-31. doi: 10.1002/(ISSN)1438-5171
Theobald J.A., Oxtoby N.S., Phillips M.A., Champness N.R., Beton P.H.. Controlling molecular deposition and layer structure with supramolecular surface assemblies[J]. Nature, 2003,424:1029-1031. doi: 10.1038/nature01915
Stepanow S., Lin N., Payer D.. Surface-assisted assembly of 2D metal-organic networks that exhibit unusual threefold coordination symmetry[J]. Angew.Chem., 2007,119:724-727. doi: 10.1002/(ISSN)1521-3757
Lingenfelder M.A., Spillmann H., Dmitriev A.. Towards surface-supported supramolecular architectures:tailored coordination assembly of 1, 4-benzenedicarboxylate and Fe on Cu(10 0)[J]. Chem.Eur.J., 2004,10:1913-1919. doi: 10.1002/(ISSN)1521-3765
Lei S.B., Tahara K., Feng X.L.. Molecular clusters in two-dimensional surface-confined nanoporous molecular networks:structure, rigidity, and dynamics[J]. J.Am.Chem.Soc., 2008,130:7119-7129. doi: 10.1021/ja800801e
Qiu X.H., Wang C., Zeng Q.D.. Alkane-assisted adsorption and assembly of phthalocyanines and porphyrins[J]. J.Am.Chem.Soc., 2000,122:5550-5556. doi: 10.1021/ja994271p
Ulman A.. Formation and structure of self-assembled monolayers[J]. Chem.Rev., 1996,96:1533-1554. doi: 10.1021/cr9502357
Li Y.B., Liu C.H., Xie Y.Z.. Temperature-controlled self-assembling structure with selective guest-recognition at the liquid-solid interface[J]. Phys. Chem.Chem.Phys., 2013,15:125-128. doi: 10.1039/C2CP43244G
Hu F.Y., Gong Y.N., Zhang X.M.. Temperature-induced transitions of self-assembled phthalocyanine molecular nanoarrays at the solid-liquid interface: from randomness to order[J]. Nanoscale, 2014,6:4243-4249. doi: 10.1039/c3nr06320h
Okawa Y., Aono M.. Linear chain polymerization initiated by a scanning tunneling microscope tip at designated positions[J]. J.Chem.Phys., 2001,115:2317-2322. doi: 10.1063/1.1384554
Li Y.B., Wan J.H., Deng K.. Transformation of self-assembled structure by the addition of active reactant[J]. J.Phys.Chem.C, 2011,115:6540-6544. doi: 10.1021/jp1097876
Mandal S.K., Okawa Y., Hasegawa T., Aono M.. Rate-determining factors in the chain polymerization of molecules initiated by local single-molecule excitation[J]. ACS Nano, 2011,5:2779-2786. doi: 10.1021/nn103231j
Katsonis N., Lubomska M., Pollard M.M., Feringa B.L., Rudolf P.. Synthetic light-activated molecular switches and motors on surfaces[J]. Prog.Surf.Sci., 2007,82:407-434. doi: 10.1016/j.progsurf.2007.03.011
Binnig G., Rohrer H., Gerber C., Weibel E.. Surface studies by scanning tunneling microscopy[J]. Phys.Rev.Lett., 1982,49:57-61. doi: 10.1103/PhysRevLett.49.57
Magonov S.N., Whangbo M.H.. Interpreting STM and AFM images[J]. Adv.Mater., 1994,6:355-371. doi: 10.1002/(ISSN)1521-4095
De Feyter S., Gesquière A., Abdel-Mottaleb M.M.. Scanning tunneling microscopy:a unique tool in the study of chirality, dynamics, and reactivity in physisorbed organic monolayers[J]. Acc.Chem.Res., 2000,33:520-531. doi: 10.1021/ar970040g
De Feyter S., De Schryver F.C.. Self-assembly at the liquid/solid interface:STM reveals[J]. J.Phys.Chem.B, 2005,109:4290-4302. doi: 10.1021/jp045298k
Zhang X.M., Zeng Q.D., Wang C.. Molecular templates and nano-reactors:two-dimensional hydrogen bonded supramolecular networks on solid/liquid interfaces[J]. RSC Adv., 2013,3:11351-11366. doi: 10.1039/c3ra40473k
Lu J., Lei S.B., Zeng Q.D.. Template-induced inclusion structures with copper(Ⅱ)phthalocyanine and coronene as guests in two-dimensional hydrogen-bonded host networks[J]. J.Phys.Chem.B, 2004,108:5161-5165.
Shen Y.T., Guan L., Zhang X.M.. Site-selective effects on guest-molecular adsorption and fabrication of four-component architecture by higher order networks[J]. Phys.Chem.Chem.Phys., 2013,15:12475-12479. doi: 10.1039/c3cp50371b
Shen Y.T., Deng K., Zeng Q.D., Wang C.. Size-selective effects on fullerene adsorption by nanoporous molecular networks[J]. Small, 2010,6:76-80. doi: 10.1002/smll.v6:1
Shen Y.T., Deng K., Zhang X.M.. Selective and competitive adsorptions of guest molecules in phase-separated networks[J]. J.Phys.Chem.C, 2011,115:19696-19701. doi: 10.1021/jp202890y
Li M., Deng K., Lei S.B.. Site-selective fabrication of two-dimensional fullerene arrays by using a supramolecular template at the liquid-solid interface[J]. Angew.Chem.Int.Ed., 2008,47:6717-6721. doi: 10.1002/anie.v47:35
Li Y.B., Ma Z., Qi G.C.. Solvent effects on supramolecular networks formed by racemic star-shaped oligofluorene studied by scanning tunneling microscopy[J]. J.Phys.Chem.C, 2008,112:8649-8653.
Wang Y.B., Niu L., Li Y.B.. Single molecule studies of cyclic peptides using molecular matrix at liquid/solid interface by scanning tunneling microscopy[J]. Langmuir, 2010,26:16305-16311. doi: 10.1021/la101467s
Shen Y.T., Zeng L.J., Lei D.. Competitive adsorption and dynamics of guest molecules in 2D molecular sieves[J]. J.Mater.Chem., 2011,21:8787-8791. doi: 10.1039/c1jm10260e
Barrett C.J., Mamiya J.I., Yager K.G., Ikeda T.. Photo-mechanical effects in azobenzene-containing soft materials[J]. Soft Matter, 2007,3:1249-1261. doi: 10.1039/b705619b
Yesodha S.K., Sadashiva Pillai C.K.. Tsutsumi N.Stable polymeric materials for nonlinear optics:a review based on azobenzene systems[J]. Prog.Polym.Sci., 2004,29:45-74. doi: 10.1016/j.progpolymsci.2003.07.002
Yager K.G., Barrett C.J.. Novel photo-switching using azobenzene functional materials[J]. J.Photochem.Photobiol.A, 2006,182:250-261. doi: 10.1016/j.jphotochem.2006.04.021
Oosaki S., Hayasaki H., Sakurai Y., Yajima S., Kimura K.. Photocontrol of ion-sensor performances in neutral-carrier-type ion sensors based on liquid-crystalline membranes[J]. Chem.Commun., 2005,522:6-522 7.
Dietrich P., Michalik F., Schmidt R.. An anchoring strategy for photoswitchable biosensor technology:azobenzene-modified SAMs on Si (111)[J]. Appl.Phys.A, 2008,93:285-292. doi: 10.1007/s00339-008-4828-0
Pijper D., Jongejan M.G.M., Meetsma A., Feringa B.L.. Light-controlled supramolecular helicity of a liquid crystalline phase using a helical polymer functionalized with a single chiroptical molecular switch[J]. J.Am.Chem.Soc., 2008,130:4541-4552. doi: 10.1021/ja711283c
Westmark P.R., Kelly J.P., Smith B.D.. Photoregulation of enzyme activity. Photochromic, transition-state-analog inhibitors of cysteine and serine proteases[J]. J.Am.Chem.Soc., 1993,115:3416-3419. doi: 10.1021/ja00062a003
Gorostiza P., Isacoff E.Y.. Optical switches for remote and noninvasive control of cell signaling[J]. Science, 2008,322:395-399. doi: 10.1126/science.1166022
Bazarnik M., Jurczyszyn L., Czajka R., Morgenstern K.. Mechanism of a molecular photo-switch adsorbed on Si(10 0)[J]. Phys.Chem.Chem.Phys., 2015,17:5366-5371. doi: 10.1039/C4CP04353G
Alemani M., Selvanathan S., Ample F.. Adsorption and switching properties of azobenzene derivatives on different noble metal surfaces:Au (111), Cu(111), and Au(1 0 0)[J]. J.Phys.Chem.C, 2008,112:10509-10514.
Mielke J., Selvanathan S., Peters M.. Molecules with multiple switching units on a Au(111) surface:self-organization and single-molecule manipulation[J]. J.Phys.:Condens.Matter, 2012,24394013. doi: 10.1088/0953-8984/24/39/394013
Shen Y.T., Guan L., Zhu X.Y., Zeng Q.D., Wang C.. Submolecular observation of photosensitive macrocycles and their isomerization effects on host-guest network[J]. J.Am.Chem.Soc., 2009,131:6174-6180. doi: 10.1021/ja808434n
Shen Y.T., Deng K., Zhang X.M.. Switchable ternary nanoporous supramolecular network on photo-regulation[J]. Nano Lett., 2011,11:3245-3250. doi: 10.1021/nl201504x
Zhang X.M., Wang S., Shen Y.T.. Two-dimensional networks of an azobenzene derivative:bi-pyridine mediation and photo regulation[J]. Nanoscale, 2012,4:5039-5042. doi: 10.1039/c2nr31186k
Kumar A.S., Ye T., Takami T.. Reversible photo-switching of single azobenzene molecules in controlled nanoscale environments[J]. Nano Lett., 2008,8:1644-1648. doi: 10.1021/nl080323+
Tsai C.S., Wang J.K., Skodje R.T., Lin J.C.. A single molecule view of bistilbene photoisomerization on a surface using scanning tunneling microscopy[J]. J.Am. Chem.Soc., 2005,127:10788-10789. doi: 10.1021/ja052448b
Shimizu H., Cojal González J.D., Hasegawa M.. Synthesis, structures, and photophysical properties of '-expanded oligothiophene 8-mers and their saturn-like C60 complexes[J]. J.Am.Chem.Soc., 2015,137:3877-3885. doi: 10.1021/jacs.5b00291
Schmidt G.M.J.. Photodimerization in the solid state[J]. Pure Appl.Chem., 1971,27:647-678.
Xue J.D., Xu J., Hu F.Y.. Highly efficient photodimerization of olefins in a nanotemplate on HOPG by scanning tunneling microscopy[J]. Phys.Chem.Chem. Phys., 2014,16:25765-25769. doi: 10.1039/C4CP04154B
Liao L.Y., Li Y.B., Zhang X.M.. STM investigation of the photoisomerization and photodimerization of stilbene derivatives on HOPG surface[J]. J.Phys.Chem. C, 2014,118:15963-15969. doi: 10.1021/jp505511e
Xu L.P., Yan C.J., Wan L.J., Jiang S.G., Liu M.H.. Light-induced structural transformation in self-assembled monolayer of 4-(amyloxy)cinnamic acid investigated with scanning tunneling microscopy[J]. J.Phys.Chem.B, 2005,109:14773-14778. doi: 10.1021/jp052959k
Tour J.M., Molecular electronics.. Synthesis and testing of components[J]. Acc. Chem.Res., 2000,33:791-804. doi: 10.1021/ar0000612
Okawa Y., Mandal S.K., Hu C.P.. Chemical wiring and soldering toward all-molecule electronic circuitry[J]. J.Am.Chem.Soc., 2011,133:8227-8233. doi: 10.1021/ja111673x
Qiao Y.H., Zeng Q.D., Tan Z.Y.. Photoinduced organic nanowires from self-assembled monolayers[J]. J.Vac.Sci.Technol.B, 2002,20:2466-2469. doi: 10.1116/1.1526601
Deshpande A., Sham C.H., Alaboson J.M.P.. Self-assembly and photopolymerization of sub-2 nm one-dimensional organic nanostructures on graphene[J]. J.Am.Chem.Soc., 2012,134:16759-16764. doi: 10.1021/ja307061e
Zhang X.M., Xu S.D., Li M.. Photo-induced polymerization and isomerization on the surface observed by scanning tunneling microscopy[J]. J. Phys.Chem.C, 2012,116:8950-8955. doi: 10.1021/jp2115884
Xu W., Zhang C., Gersen H.. A molecular conformational change induced self-assembly:from randomness to order[J]. Chem.Commun., 2013,49:5207-5209. doi: 10.1039/c3cc40743h
Darwish N., Aragones A.C., Darwish T., Ciampi S., Díez-Pérez I.. Multi-responsive photo-and chemo-electrical single-molecule switches[J]. Nano Lett., 2014,14:7064-7070. doi: 10.1021/nl5034599
Katsonis N., Kudernac T., Walko M.. Reversible conductance switching of single diarylethenes on a gold surface[J]. Adv.Mater., 2006,18:1397-1400. doi: 10.1002/(ISSN)1521-4095
Frath D., Sakano T., Imaizumi Y.. Diarylethene self-assembled monolayers:cocrystallization and mixing-induced cooperativity highlighted by scanning tunneling microscopy at the liquid/solid interface[J]. Chem.Eur.J., 2015,21:11350-11358. doi: 10.1002/chem.201500804
Oreshkin I., Panov V.I., Vasil'ev S.I., Koroteev N.I., Magnitskii S.A.. Direct STM observation of electronic structure modification of naphthacenequinone molecules due to photoisomerization[J]. J.Exp.Theor.Phys.Lett., 1998,68:521-526. doi: 10.1134/1.567900
Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
Yutong Xiong , Ting Meng , Wendi Luo , Bin Tu , Shuai Wang , Qingdao Zeng . Molecular conformational effects on co-assembly systems of low-symmetric carboxylic acids investigated by scanning tunneling microscopy. Chinese Journal of Structural Chemistry, 2025, 44(2): 100511-100511. doi: 10.1016/j.cjsc.2025.100511
Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
Sixiao Liu , Tianyi Wang , Lei Zhang , Chengyin Wang , Huan Pang . Cerium-based metal-organic framework-modified natural mineral vermiculite for photocatalytic nitrogen fixation under visible-light irradiation. Chinese Chemical Letters, 2025, 36(3): 110058-. doi: 10.1016/j.cclet.2024.110058
Man Wu , Chuandong Jia . A light-powered molecular pump achieving transmembrane concentration gradient. Chinese Journal of Structural Chemistry, 2025, 44(4): 100452-100452. doi: 10.1016/j.cjsc.2024.100452
Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M2L4 coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
Jieqiong Qin , Zhi Yang , Jiaxin Ma , Liangzhu Zhang , Feifei Xing , Hongtao Zhang , Shuxia Tian , Shuanghao Zheng , Zhong-Shuai Wu . Interfacial assembly of 2D polydopamine/graphene heterostructures with well-defined mesopore and tunable thickness for high-energy planar micro-supercapacitors. Chinese Chemical Letters, 2024, 35(7): 108845-. doi: 10.1016/j.cclet.2023.108845