Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers
Source abstract
Abstract
Abstract The supramolecular self-assembly of a push-pull dye is investigated using scanning tunneling microscopy (STM) at the liquid–solid interface. The molecule has an indandione head, a bithiophene backbone and a triphenylamine–bithiophene moiety functionalized with two carboxylic acid groups as a tail. The STM images show that the molecules adopt an “L” shape on the surface and form chiral Baravelle spiral triangular trimers at low solution concentrations. The assembly of these triangular chiral trimers on the graphite surface results in the formation of two types of chiral Kagomé nanoarchitectures. The Kagomé-α structure is composed of only one trimer enantiomer, whereas the Kagomé-β structure results from the arrangement of two trimer enantiomers in a 1:1 ratio. These Kagomé lattices are stabilized by intermolecular O-H···O hydrogen bonds between carboxylic acid groups. These observations reveal that the complex structure of the push-pull dye molecule leads to the formation of sophisticated two-dimensional chiral Kagomé nanoarchitectures. The subsequent deposition of coronene molecules leads to the disappearance of the Kagomé-β structure, whereas the Kagomé-α structure acts as the host template to trap the coronene molecules.
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OpenAlex topics: Surface Chemistry and Catalysis · Photonic Crystals and Applications · Graphene research and applications
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References (61)
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1. Seibel, J., Zoppi, L. & Ernst, K.-H. 2D conglomerate crystallization of heptahelicene. Chem. Commun. 50, 8751–8753 (2014).10.1039/C4CC03574G ↗
2. Yang, L., Tan, X., Wang, Z. & Zhang, X. Supramolecular polymers: historical development, preparation, characterization, and functions. Chem. Rev. 115, 7196–7239 (2015).10.1021/cr500633b ↗
3. Stepanenko, V., Kandanelli, R., Uemura, S., Würthner, F. & Fernández, G. Concentration-dependent rhombitrihexagonal tiling patterns at the liquid/solid interface. Chem. Sci. 6, 5853–5858 (2015).10.1039/C5SC00811E ↗
4. Nguyen, V. Q. et al. Unprecedented self-organized monolayer of a Ru(II) complex by diazonium electroreduction. J. Am. Chem. Soc. 138, 9381–9384 (2016).10.1021/jacs.6b04827 ↗
5. Zhang, L. et al. Site- and configuration-selective anchoring of iron-phthalocyanine on the step edges of Au(111) surface. J. Phys. Chem. C 115, 10791–10796 (2011).10.1021/jp203046b ↗
6. Seljamäe-Green, R. T. et al. Formation of bioinorganic complexes by the corrosive adsorption of (S)-proline on Ni/Au(111). Langmuir 31, 262–271 (2015).10.1021/la504236w ↗
7. Silly, F. et al. Melamine structures on the Au(111) surface. J. Phys. Chem. C 112, 11476–11480 (2008).10.1021/jp8033769 ↗
8. Skomski, D. et al. High-fidelity self-assembly of crystalline and parallel-oriented organic thin films by Π-Π stacking from a metal surface. Langmuir 30, 10050–10056 (2014).10.1021/la502288v ↗
9. Maeda, H. Supramolecular chemistry of pyrrole-based Π-conjugated. Molecules. B Chem. Soc. Jpn 86, 1359–1399 (2013).10.1246/bcsj.20130219 ↗
10. Silly, F. Selecting two-dimensional halogen-halogen bonded self-assembled 1,3,5-tris(4- iodophenyl) benzene porous nanoarchitectures at the solid-liquid interface. J. Phys. Chem. C 117, 20244–20249 (2013).10.1021/jp4057626 ↗
11. Liu, J. et al. Solvent-controlled 2D host-guest (2,7,12-trihexyloxytruxene/coronene) molecular nanostructures at organic liquid/solid interface investigated by scanning tunneling microscopy. Langmuir 26, 8195–8200 (2010).10.1021/la904568q ↗
12. Yue, J.-Y.; Liu, X.-H.; Sun, B.; Wang, D. The on-surface synthesis of imine-based covalent organic frameworks with non-aromatic linkage. Chem. Commun. 51, 14318–14321 (2015).10.1039/C5CC05689F ↗
13. Wu, R. et al. Self-assembled patterns and young´s modulus of single-layer naphthalocyanine molecules on Ag(111). J. Phys. Chem. C 119, 8208–8212 (2015).10.1021/acs.jpcc.5b01344 ↗
14. Qing, H. et al. Atomic force microscopy investigation of growth process of organic TCNQ aggregates on SiO2 and mica substrates. Chin. Phys. B 19, 080517 (2010).10.1088/1674-1056/19/8/080517 ↗
15. Uemura, S., Aono, M., Sakata, K., Komatsu, T. & Kunitake, M. Thermodynamic control of 2D bicomponent porous networks of melamine and melem: diverse hydrogen-bonded networks. J. Phys. Chem. C 117, 24815–24821 (2013).10.1021/jp406810c ↗
16. Rosei, F. et al. Properties of large organic molecules on metal surfaces. Progr. Surf. Sci. 71, 95–146 (2003).10.1016/S0079-6816(03)00004-2 ↗
17. Yagai, S. Supramolecularly engineered functional Π-assemblies based on complementary hydrogen-bonding interactions. Bull. Chem. Soc. Jpn 88, 28–58 (2015).10.1246/bcsj.20140261 ↗
18. Yang, Y. & Wang, C. Hierarchical construction of self-assembled low-dimensional molecular architectures observed by using scanning tunneling microscopy. Chem. Soc. Rev. 38, 2576 (2009).10.1039/b807500j ↗
19. Yan, H. et al. Rationalization of the selectivity in the optimization of processing conditions for high-performance polymer solar cells based on the polymer self-assembly ability. J. Phys. Chem. C 118, 29473–29481 (2014).10.1021/jp5075797 ↗
20. Chen, L.-M., Hong, Z., Li, G. & Yang, Y. Recent progress in polymer solar cells: manipulation of polymer: fullerene morphology and the formation of efficient inverted polymer solar cells. Adv. Mater. 21, 1434–1449 (2009).10.1002/adma.200802854 ↗
21. Fitzner, R. et al. Interrelation between crystal packing and small-molecule organic solar cell performance. Adv. Mater. 24, 675–680 (2012).10.1002/adma.201104439 ↗
22. Qin, P. et al. Design of an organic chromophore for p-type dye-sensitized solar cells. J. Am. Chem. Soc. 130, 8570–8571, 00322 (2008).10.1021/ja8001474 ↗
23. Li, L., et al. Double-layered NiO photocathodes for p-Type DSSCs with record IPCE. Adv. Mater. 22, 1759–1762 (2010).10.1002/adma.200903151 ↗
24. Li, F. et al. Organic dye-sensitized tandem photoelectrochemical cell for light driven total water splitting. J. Am. Chem. Soc. 137, 9153–9159 (2015).10.1021/jacs.5b04856 ↗
25. Benazzi, E., Mallows, J., Summers, G. H., Black, F. A. & Gibson, E. A. Developing photocathode materials for p-type dye-sensitized solar cells. J. Mater. Chem. C 7, 10409–10445 (2019).10.1039/C9TC01822K ↗
26. Gibson, E. A. Dye-sensitizedphotocathodes for H2 evolution. Chem. Soc. Rev. 46, 6194–6209 (2017).10.1039/C7CS00322F ↗
27. Yagai, S. et al. Self-organization of hydrogen-bonding naphthalene chromophores into j-type nanorings and h-type nanorods: impact of regioisomerism. Angew. Chem. Int. Ed. 51, 6643–6647 (2012).10.1002/anie.201201436 ↗
28. Barth, J. V. et al. Building supramolecular nanostructures at surfaces by hydrogen bonding. Angew. Chem. Int. Ed. 39, 1230–1234 (2000).10.1002/(SICI)1521-3773(20000403)39:7<1230::AID-ANIE1230>3.0.CO;2-I ↗
29. Barth, J. V. Molecular architectonic on metal surfaces. Annu. Rev. Phys. Chem. 58, 375–407 (2007).10.1146/annurev.physchem.56.092503.141259 ↗
30. Feyter, S. D. & Schryver, F. C. D. Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy. Chem. Soc. Rev. 32, 139–150 (2003).10.1039/b206566p ↗
31. Bonifazi, D., Mohnani, S. & Llanes-Pallas, A. Supramolecular chemistry at interfaces: molecular recognition on nanopatterned porous surfaces. Chem. Eur. J. 15, 7004–7025 (2009).10.1002/chem.200900900 ↗
32. Xu, W. et al. Cyanuric acid and melamine on Au(111): structure and energetics of hydrogen-bonded networks. Small 3, 854–858 (2007).10.1002/smll.200600407 ↗
33. Xu, L. et al. Chiral transition of the supramolecular assembly by concentration modulation at the liquid/solid interface. J. Phys. Chem. C 119, 17920–17929 (2015).10.1021/acs.jpcc.5b04799 ↗
34. Xu, L. et al. Concentration-dependent structure and structural transition from chirality to nonchirality at the liquid/solid interface by coassembly. Nanoscale 7, 11734–11745 (2015).10.1039/C5NR03142G ↗
35. Zentner, C. A. et al. High surface area and Z in a thermally stable 8-fold polycatenated hydrogen-bonded framework. Chem. Commun. 51, 11642–11645 (2015).
36. Zhang, X., Zeng, Q. & Wang, C. Molecular templates and nano-reactors: two-dimensional hydrogen bonded supramolecular networks on solid/liquid interfaces. RSC Adv. 3, 11351–11366 (2013).10.1039/c3ra40473k ↗
37. Zhou, H. & Wuest, J. D. Crankshafts: using simple, flat C2h-symmetric molecules to direct the assembly of chiral 2D nanopatterns. Langmuir 29, 7229–7238 (2013).10.1021/la303659c ↗
38. Hu, F.-Y. et al. In situ STM investigation of two-dimensional chiral assemblies through Schiff-base condensation at a liquid/solid interface. ACS Appl. Mater. Inter. 5, 1583–1587 (2013).10.1021/am303236w ↗
39. Suh, M. P., Cheon, Y. E. & Lee, E. Y. Syntheses and functions of porous metallosupramolecular networks. Coord. Chem. Rev. 252, 1007–1026 (2008).10.1016/j.ccr.2008.01.032 ↗
40. Silly, F. Two-dimensional 1,3,5-tris(4-carboxyphenyl)benzene self-assembly at the 1- phenyloctane/graphite interface revisited. J. Phys. Chem. C 116, 10029–10032 (2012).10.1021/jp300678m ↗
41. Miao, K. et al. Hydroxyl versus carboxyl substituent: effects of competitive and cooperative multiple hydrogen bonds on concentration-controlled self-assembly. J. Phys. Chem. C 120, 14187–14197 (2016).10.1021/acs.jpcc.6b03920 ↗
42. Chen, T., Chen, Q., Zhang, X., Wang, D. & Wan, L.-J. Chiral Kagomé network from thiacalix[4]arene tetrasulfonate at the interface of aqueous solution/Au(111) surface: an in situ electrochemical scanning tunneling microscopy study. J. Am. Chem. Soc. 132, 5598–5599 (2010).10.1021/ja101598p ↗
43. Mo, Y.-P., Liu, X.-H. & Wang, D. Concentration-directed polymorphic surface covalent organic frameworks: rhombus, parallelogram, and Kagomé. ACS Nano 11, 11694–11700 (2017).10.1021/acsnano.7b06871 ↗
44. Furukawa, S. et al. Molecular geometry directed Kagomé and honeycomb networks: toward two-dimensional crystal engineering. J. Am. Chem. Soc. 128, 3502–3503 (2006).10.1021/ja0583362 ↗
45. Tahara, K. et al. Harnessing by a diacetylene unit: a molecular design for porous two-dimensional network formation at the liquid/solid interface. Chem. Commun. 50, 2831–2833 (2014).10.1039/c3cc47949h ↗
46. Furukawa, S. et al. Structural transformation of a two-dimensional molecular network in response to selective guest inclusion. Angew. Chem., Int. Ed. 46, 2831–2834 (2007).10.1002/anie.200604782 ↗
47. Brisse, R. et al. A red to blue series of push-pull dyes for NiO based p-DSSCs. Sustain. Energy Fuels 2, 648–654 (2018).10.1039/C7SE00474E ↗
48. Silly, F. A robust method for processing scanning probe microscopy images and determining nanoobject position and dimensions. J. Microsc. 236, 211–218 (2009).10.1111/j.1365-2818.2009.03191.x ↗
49. Dienstmaier, J. F. et al. On the scalability of supramolecular networks - high packing density vs optimized hydrogen bonds in tricarboxylic acid monolayers. Langmuir 26, 10708–10716 (2010).10.1021/la101634w ↗
50. Li, X. et al. Adsorption and self-assembly of the 2,3,5,6-tetra(2-pyridyl)pyrazine nonplanar molecule on a au(111) surface. J. Phys. Chem. C 120, 6039–6049 (2016).10.1021/acs.jpcc.5b12163 ↗
51. Hooper, J. et al. Chiral surface networks of 3-HPLN – a molecular analog of rounded triangle assembly. Surf. Sci. 629, 65–74 (2014).10.1016/j.susc.2014.04.015 ↗
52. Azumi, R., Götz, G., Debaerdemaeker, T. & Bäuerle, P. Coincidence of the molecular organization of β-substituted oligothiophenes in two-dimensional layers and three-dimensional crystals. Chem. Eur. J. 6, 735–744 (2000).10.1002/(SICI)1521-3765(20000218)6:4<735::AID-CHEM735>3.0.CO;2-A ↗
53. Müller, H. et al. Influence of polar substituents on the epitaxy of oligothiophenes on graphite: a systematic STM investigation. Adv. Mater. 8, 733–737 (1996).10.1002/adma.19960080905 ↗
54. Abdel-Mottaleb, M. M. S., Götz, G., Kilickiran, P., Bäuerle, P. & Mena-Osteritz, E. Influence of halogen substituents on the self-assembly of oligothiophenes-a combined STM and theoretical approach. Langmuir 22, 1443–1448 (2006).10.1021/la052566c ↗
55. Stecher, R., Gompf, B., Münter, J. S. R. & Effenberger, F. Monolayers of functionalized oligothiophenes on graphite-STM investigation of the influence of intermolecular interactions on the epitaxy. Adv. Mater. 11, 927–931 (1999).10.1002/(SICI)1521-4095(199908)11:11<927::AID-ADMA927>3.0.CO;2-D ↗
56. Cicoira, F., Miwa, J. A., Melucci, M., Barbarella, G. & Rosei, F. Ordered assembly of α-quinquethiophene on a copper oxide nanotemplate. Small 2, 1366–1371 (2006).10.1002/smll.200600057 ↗
57. Yang, Z.-Y. et al. Scanning tunneling microscopy of the formation, transformation, and property of oligothiophene self-organizations on graphite and gold surfaces. Proc. Natl Acad. Sci. USA 104, 3707–3712 (2007).10.1073/pnas.0611585104 ↗
58. Lu, J. et al. Template-induced inclusion structures with copper(II) phthalocyanine and coronene as guests in two-dimensional hydrogen-bonded host networks. J. Phys. Chem. B 108, 5161–5165 (2004).10.1021/jp037508j ↗
59. Perepichka, I. F.; Perepichka, D. F. Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, Vol 2 (John Wiley & Sons, 2009).10.1002/9780470745533 ↗
60. Mishra, A., Ma, C.-Q. & Bäuerle, P. Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. Chem. Rev. 109, 1141–1276 (2009).10.1021/cr8004229 ↗
61. Ouchi, H. et al. Impact of helical organization on the photovoltaic properties of oligothiophene supramolecular polymers. Chem. Sci. 9, 3638–3643 (2018).10.1039/C7SC05093C ↗