Citation: Liu Yuqing, Santella Marco, Fan Zhiqiang, Wang Xintai, Jiang Xiangwei, Nielsen Mogens Brøndsted, Nørgaard Kasper, Laursen Bo W., Li Jingbo, Wei Zhongming. Diamine anchored molecular junctions of oligo(phenylene ethynylene) cruciform[J]. Chinese Chemical Letters, ;2018, 29(2): 271-275. doi: 10.1016/j.cclet.2017.08.034 shu

Diamine anchored molecular junctions of oligo(phenylene ethynylene) cruciform

a.
State Key Laboratory of Superlattices and Microstructures, Institute of Semiconductors, Chinese Academy of Sciences, Beijing 100083, China
b.
Sino-Danish College, University of Chinese Academy of Science, Beijing 100049, China
c.
Nano-Science Center and Department of Chemistry, University of Copenhagen, Copenhagen DK-2100, Denmark
d.
Sino-Danish Center for Education and Research, Beijing 100049, China

Corresponding author: Wei Zhongming, zmwei@semi.ac.cn
Received Date: 13 June 2017
Revised Date: 9 August 2017
Accepted Date: 15 August 2017
Available Online: 3 March 2017

Figures(4)

Using diamine as anchoring group, the self-assembled monolayers (SAMs) based on oligo(phenyleneethynylene)s (OPEs) and cruciform OPEs with an extended tetrathiafulvalene (TTF) (OPE3 and OPE3-TTF) were successfully formed on the Au substrate. The uniformity and stability of SAMs were confirmed through cyclic voltammetry (CV) and electrochemical reductive desorption. The investigation of transport properties of SAMs was achieved by conducting-probe atomic force microscopy (CP-AFM) with both Au and Pt tips. The results indicated that the conductance of OPE3-TTF was 17 and 46 times that of OPE3 for Au and Pt tips, respectively. Theoretical calculations are qualitatively consistent with the experimental results, suggesting that the diamine as anchoring group has a great potential in molecular electronics.
- Oligo(phenylene-ethynylene),
- Tetrathiafulvalene,
- Diamine,
- Molecular electronics,
- Cruciform
1. [1]
  K. Moth-Poulsen, T. Bjørnholm, Nat. Nanotechnol. 4(2009) 551-556. doi: 10.1038/nnano.2009.176
2. [2]
  H. Song, M.A. Reed, T. Lee, Adv. Mater. 23(2011) 1583-1608. doi: 10.1002/adma.201004291
3. [3]
  T. Li, M. Jevric, J.R. Hauptmann, et al., Adv. Mater. 25(2013) 4164-4170. doi: 10.1002/adma.201300607
4. [4]
  Z. Zhang, T. Li, Chin. Chem. Lett. 27(2016) 1209-1222. doi: 10.1016/j.cclet.2016.05.031
5. [5]
  D. Xiang, X. Wang, C. Jia, T. Lee, X. Guo, Chem. Rev. 116(2016) 4318-4440. doi: 10.1021/acs.chemrev.5b00680
6. [6]
  A. Cui, H. Dong, W. Hu, Small 11(2015) 6115-6141. doi: 10.1002/smll.v11.46
7. [7]
  C. Jia, A. Migliore, N. Xin, et al., Science 352(2016) 1443-1445. doi: 10.1126/science.aaf6298
8. [8]
  A. Cornia, P. Seneor, Nat. Mater. 16(2017) 505-506. doi: 10.1038/nmat4900
9. [9]
  M. Cinchetti, V.A. Dediu, L.E. Hueso, Nat. Mater. 16(2017) 507-515. doi: 10.1038/nmat4902
10. [10]
  J. Dong, H. Zhang, Chin. Chem. Lett. 27(2016) 1097-1104. doi: 10.1016/j.cclet.2016.05.005
11. [11]
  Y. Zhen, H. Dong, L. Jiang, W. Hu, Chin. Chem. Lett. 27(2016) 1330-1338. doi: 10.1016/j.cclet.2016.06.023
12. [12]
  T. Li, W. Hu, D. Zhu, Adv. Mater. 22(2010) 286-300. doi: 10.1002/adma.v22:2
13. [13]
  J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo, G.M. Whitesides, Chem. Rev. 105(2005) 1103-1170. doi: 10.1021/cr0300789
14. [14]
  P. Moreno-García, M. Gulcur, D.Z. Manrique, et al., J. Am. Chem. Soc.135(2013) 12228-12240. doi: 10.1021/ja4015293
15. [15]
  A. Tan, J. Balachandran, S. Sadat, et al., J. Am. Chem. Soc.133(2011) 8838-8841. doi: 10.1021/ja202178k
16. [16]
  F. Chen, X. Li, J. Hihath, Z. Huang, N. Tao, J. Am. Chem. Soc. 128(2006) 15874-15881. doi: 10.1021/ja065864k
17. [17]
  C.A. Martin, D. Ding, J.K. Sørensen, et al., J. Am. Chem. Soc. 130(2008) 13198-13199. doi: 10.1021/ja804699a
18. [18]
  L. Venkataraman, J.E. Klare, I.W. Tam, et al., Nano Lett. 6(2006) 458-462. doi: 10.1021/nl052373+
19. [19]
  I.S. Kristensen, D.J. Mowbray, K.S. Thygesen, K.W. Jacobsen, J. Phys.:Condens. Matter 20(2008) 374101. doi: 10.1088/0953-8984/20/37/374101
20. [20]
  M.S. Hybertsen, L. Venkataraman, J.E. Klare, et al., J. Phys.:Condens. Matter 20(2008) 374115. doi: 10.1088/0953-8984/20/37/374115
21. [21]
  Q. Lu, K. Liu, H. Zhang, et al., ACS Nano 3(2009) 3861-3868. doi: 10.1021/nn9012687
22. [22]
  W. Hong, D.Z. Manrique, P. Moreno-García, et al., J. Am. Chem. Soc. 134(2012) 2292-2304. doi: 10.1021/ja209844r
23. [23]
  M.T. González, A. Díaz, E. Leary, et al., J. Am. Chem. Soc.135(2013) 5420-5426. doi: 10.1021/ja312392q
24. [24]
  M.T. González, X. Zhao, D.Z. Manrique, et al., J. Phys. Chem. C 118(2014) 21655-21662. doi: 10.1021/jp506078a
25. [25]
  C. Jia, J. Wang, C. Yao, et al., Angew. Chem. Int. Ed. 52(2013) 8666-8670. doi: 10.1002/anie.201304301
26. [26]
  Y. Cao, S. Dong, S. Liu, et al., Angew. Chem. Int. Ed. 51(2012) 12228-12232. doi: 10.1002/anie.v51.49
27. [27]
  X. Guo, Adv. Mater. 25(2013) 3397-3408. doi: 10.1002/adma.v25.25
28. [28]
  X. Guo, A.A. Gorodetsky, J. Hone, J.K. Barton, C. Nuckolls, Nat. Nanotechnol. 3(2008) 163-167. doi: 10.1038/nnano.2008.4
29. [29]
  S. Liu, G.H. Clever, Y. Takezawa, et al., Angew. Chem. Int. Ed. 50(2011) 8886-8890. doi: 10.1002/anie.v50.38
30. [30]
  H. Wen, W. Li, J. Chen, et al., Sci. Adv. 2(2016) e1601113. doi: 10.1126/sciadv.1601113
31. [31]
  C. Jia, J. Wang, C. Yao, Y. Cao, et al., Angew. Chem. Int. Ed. 52(2013) 8666-8670. doi: 10.1002/anie.201304301
32. [32]
  L. Gao, L.-L. Li, X. Wang, et al., Chem. Sci. 6(2015) 2469-2473. doi: 10.1039/C4SC03612C
33. [33]
  L.A. Bumm, J.J. Arnold, M.T. Cygan, et al., Science 271(1996) 1705-1707. doi: 10.1126/science.271.5256.1705
34. [34]
  J.L. Zhang, J.Q. Zhong, J.D. Lin, et al., Chem. Soc. Rev. 44(2015) 2998-3022. doi: 10.1039/C4CS00377B
35. [35]
  L.J. Wang, A. Yong, K.G. Zhou, et al., Chem.-Asian J. 8(2013) 1901-1909. doi: 10.1002/asia.v8.8
36. [36]
  Z.J. Donhauser, B.A. Mantooth, K.F. Kelly, et al., Science 292(2001) 2303-2307. doi: 10.1126/science.1060294
37. [37]
  S.H. Choi, C.D. Frisbie, J. Am. Chem. Soc. 132(2010) 16191-16201. doi: 10.1021/ja1060142
38. [38]
  J. Liao, J.S. Agustsson, S. Wu, et al., Nano Lett. 10(2010) 759-764. doi: 10.1021/nl902000e
39. [39]
  M. Vestergaard, K. Jennum, J.K. Sørensen, K. Kilså, M.B. Nielsen, J. Org. Chem. 73(2008) 3175-3183. doi: 10.1021/jo702735d
40. [40]
  J.K. Sørensen, M. Vestergaard, A. Kadziola, K. Kilså, M.B. Nielsen, Org. Lett. 8(2006) 1173-1176. doi: 10.1021/ol060071o
41. [41]
  H. Lissau, R. Frisenda, S.T. Olsen, et al., Nat. Commun. 6(2015) 10233-10240. doi: 10.1038/ncomms10233
42. [42]
  K. Jennum, M. Vestergaard, A.H. Pedersen, et al., Synthesis 4(2011) 539-548.
43. [43]
  Z. Wei, T. Li, K. Jennum, et al., Langmuir 28(2012) 4016-4023. doi: 10.1021/la204340n
44. [44]
  C.R. Parker, Z. Wei, C.R. Arroyo, et al., Adv. Mater. 25(2013) 405-409. doi: 10.1002/adma.201201583
45. [45]
  C.R.Parker, E.Leary, R.Frisenda, etal., J.Am.Chem.Soc.136(2014)16497-16507. doi: 10.1021/ja509937k
46. [46]
  Z. Wei, T. Hansen, M. Santella, et al., Adv. Funct. Mater. 25(2015) 1700-1708. doi: 10.1002/adfm.201404388
47. [47]
  Z. Wang, H. Dong, T. Li, et al., Nat. Commun. 6(2015) 8478-8487. doi: 10.1038/ncomms9478
48. [48]
  Y. Kim, T.J. Hellmuth, M. Buerkle, F. Pauly, E. Scheer, ACS Nano 5(2011) 4104-4111. doi: 10.1021/nn200759s
49. [49]
  D. Kruger, R. Rousseau, H. Fuchs, D. Marx, Angew. Chem. Int. Ed. 42(2003) 2251-2253. doi: 10.1002/anie.200351000
50. [50]
  S.Y. Quek, L. Venkataraman, H.J. Choi, et al., Nano Lett. 7(2007) 3477-3482. doi: 10.1021/nl072058i
51. [51]
  H. Valkenier, E.H. Huisman, P.A. van Hal, et al., J. Am. Chem. Soc. 133(2011) 4930-4939. doi: 10.1021/ja110358t
52. [52]
  D. Fracasso, H. Valkenier, J.C. Hummelen, G.C. Solomon, R.C. Chiechi, J. Am. Chem. Soc. 133(2011) 9556-9563. doi: 10.1021/ja202471m
53. [53]
  J. Taylor, H. Guo, J. Wang, Phys. Rev. B 63(2001) 245407-245419. doi: 10.1103/PhysRevB.63.245407
54. [54]
  M. Brandbyge, J.L. Mozos, P. Ordejon, J. Taylor, K. Stokbro, Phys. Rev. B 65(2002) 165401-165417. doi: 10.1103/PhysRevB.65.165401
55. [55]
  M. Buttiker, Y. Imry, R. Landauer, S. Pinhas, Phys. Rev. B 31(1985) 6207-6215. doi: 10.1103/PhysRevB.31.6207
56. [56]
  J. Fock, M. Leijnse, K. Jennum, et al., Phys. Rev. B 86(2012) 6244-6247.
1. [1]
  Salim Ullah , Jianliang Shen , Hong-Tao Xu . Innovative self-healing conductive organogel: Pioneering the future of electronics. Chinese Chemical Letters, 2025, 36(3): 110553-. doi: 10.1016/j.cclet.2024.110553
2. [2]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
3. [3]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
4. [4]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
5. [5]
  Yanwei Duan , Qing Yang . Molecular targets and their application examples for interrupting chitin biosynthesis. Chinese Chemical Letters, 2025, 36(4): 109905-. doi: 10.1016/j.cclet.2024.109905
6. [6]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
7. [7]
  Li Lin , Song-Lin Tian , Zhen-Yu Hu , Yu Zhang , Li-Min Chang , Jia-Jun Wang , Wan-Qiang Liu , Qing-Shuang Wang , Fang Wang . Molecular crowding electrolytes for stabilizing Zn metal anode in rechargeable aqueous batteries. Chinese Chemical Letters, 2024, 35(7): 109802-. doi: 10.1016/j.cclet.2024.109802
8. [8]
  Minghao Hu , Tianci Xie , Yuqiang Hu , Longjie Li , Ting Wang , Tongbo Wu . Allosteric DNAzyme-based encoder for molecular information transfer. Chinese Chemical Letters, 2024, 35(7): 109232-. doi: 10.1016/j.cclet.2023.109232
9. [9]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
10. [10]
  Wei-Jia Wang , Kaihong Chen . Molecular-based porous polymers with precise sites for photoreduction of carbon dioxide. Chinese Chemical Letters, 2025, 36(1): 109998-. doi: 10.1016/j.cclet.2024.109998
11. [11]
  Dongpu Wu , Zheng Yang , Yuchen Xia , Lulu Wu , Yingxia Zhou , Caoyuan Niu , Puhui Xie , Xin Zheng , Zhanqi Cao . Surface controllable wettability using amphiphilic rotaxane molecular shuttles. Chinese Chemical Letters, 2025, 36(2): 110353-. doi: 10.1016/j.cclet.2024.110353
12. [12]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
13. [13]
  Kai Ye , Zhicheng Ye , Chuantao Wang , Zhilai Luo , Cheng Lian , Chunyan Bao . Artificial signal transduction triggered by molecular photoisomerization in lipid membranes. Chinese Chemical Letters, 2025, 36(4): 110033-. doi: 10.1016/j.cclet.2024.110033
14. [14]
  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
15. [15]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
16. [16]
  Qihan Lin , Jiabin Xing , Yue-Yang Liu , Gang Wu , Shi-Jia Liu , Hui Wang , Wei Zhou , Zhan-Ting Li , Dan-Wei Zhang . taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119
17. [17]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
18. [18]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
19. [19]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
20. [20]
  Ruonan Guo , Heng Zhang , Changsheng Guo , Ningqing Lv , Beidou Xi , Jian Xu . Degradation of neonicotinoids with different molecular structures in heterogeneous peroxymonosulfate activation system through different oxidation pathways. Chinese Chemical Letters, 2024, 35(9): 109413-. doi: 10.1016/j.cclet.2023.109413

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(686)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142