Citation: Lu Wang, Kai-Qi Ye, Hong-Yu Zhang. Organic materials with hydrostatic pressure induced mechanochromic properties[J]. Chinese Chemical Letters, ;2016, 27(8): 1367-1375. doi: 10.1016/j.cclet.2016.06.049 shu

Organic materials with hydrostatic pressure induced mechanochromic properties

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China

Corresponding author: Kai-Qi Ye, yekq@lu.edu.cn Hong-Yu Zhang, hongyuzhang@jlu.edu.cn
Received Date: 29 April 2016
Revised Date: 21 June 2016
Accepted Date: 21 June 2016
Available Online: 27 August 2016

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Mechanochromic organic materials are a typical class of stimuli materials that has response to external physical stimuli such as shearing, grinding, and compressing etc. Organic compounds with mechanochromic characters in solid forms have attracted significant attention in the past decades due to their potential applications in sensors and memory devices. Diamond anvil cell is an emerging technology that can provide isotropic pressure in a tiny place. Thus a new stimuli method can be applied in investigating optical variation of mechanochromic materials. In this review, we focus on mechanoluminescence systems that are responsive to isotropic compression under high pressure and summarize the recent advances on organic materials studied by the diamond anvil cell.
- Organic solids,
- Mechanochromic,
- Diamond anvil cell,
- Stimuli response,
- Hydrostatic pressure
1. [1]
  Y.Q. Dong, J.W.Y. Lam, B.Z. Tang. Mechanochromic luminescence of aggregationinduced emission Luminogens[J]. J. Phys. Chem. Lett., 2015,6:3429-3436. doi: 10.1021/acs.jpclett.5b01090
2. [2]
  X.Y. Mu, D. Liu, X. Cheng. AuI AuI interaction induced semiconducting microwires with photo- and vapor-responsive properties[J]. Org. Electron., 2012,13:457-463. doi: 10.1016/j.orgel.2011.11.013
3. [3]
  J. Feng, K.J. Tian, D.H. Hu. A triarylboron-based fluorescent thermometer: sensitive over a wide temperature range, Angew[J]. Angew. Chem. Int. Ed., 2011,50:8072-8076. doi: 10.1002/anie.v50.35
4. [4]
  T. Sato, M. Higuchi. A vapoluminescent Eu-based metallo-supramolecular polymer[J]. Chem. Commun., 2012,48:4947-4949. doi: 10.1039/c2cc30972f
5. [5]
  W.R. Browne, M.M. Pollard, B. de Lange, A. Meetsma, B.L. Feringa. Reversible threestate switching of luminescence: a new twist to electro- and photochromic behavior[J]. J. Am. Chem. Soc., 2006,128:12412-12413. doi: 10.1021/ja064423y
6. [6]
  X. Cheng, K. Wang, S. Huang. Organic crystals with near-infrared amplified spontaneous emissions based on 2'-hydroxychalcone derivatives: subtle structure modification but great property change[J]. Angew. Chem. Int. Ed., 2015,54:8369-8373. doi: 10.1002/anie.201503914
7. [7]
  K. Wang, H.Y. Zhang, S.Y. Chen. Organic polymorphs: one-compound-based crystals with molecular-conformation- and packing-dependent luminescent properties[J]. Adv. Mater., 2014,26:6168-6173. doi: 10.1002/adma.201401114
8. [8]
  X. Cheng, D. Li, Z.Y. Zhang, H.Y. Zhang, Y. Wang. Organoboron compounds with morphology-dependent NIR emissions and dual-channel fluorescent ON/OFF switching[J]. Org. Lett., 2014,16:880-883. doi: 10.1021/ol403639n
9. [9]
  B.L. Tang, H.P. Liu, F. Li, Y. Wang, H.Y. Zhang. Single-benzene solid emitters with lasing properties based on aggregation-induced emissions[J]. Chem. Commun., 2016,52:6577-6580. doi: 10.1039/C6CC02616H
10. [10]
  X. Cheng, Y.F. Zhang, S.H. Han. Multicolor amplified spontaneous emissions based on organic polymorphs that undergo excited-state intramolecular proton transfer[J]. Chem. Eur. J., 2016,22:4899-4903. doi: 10.1002/chem.v22.14
11. [11]
  J.A. Xu, H.K. Mao, P.M. Bell. High-pressure ruby and diamond fluorescence: observations at 0.21 to 0.55 terapascal[J]. Science, 1986,32:1404-1406.
12. [12]
  L. Dubrovinsky, N. Dubrovinskaia, V.B. Prakapenka, A.M. Abakumov. Implementation of micro-ball nanodiamond anvils for high-pressure studies above 6 Mbar[J]. Nat. Commun., 2012,31163. doi: 10.1038/ncomms2160
13. [13]
  K. Wang, S.R. Li, X. Tan. High pressure supramolecular chemistry[J]. Chin. Sci. Bull., 2014,59:5258-5268. doi: 10.1007/s11434-014-0615-9
14. [14]
  R. Lee, J.A.K. Howard, M.R. Probert, J.W. Steed. Structure of organic solids at low temperature and high pressure[J]. Chem. Soc. Rev., 2014,43:4300-4311. doi: 10.1039/c4cs00046c
15. [15]
  D. Li, H.Y. Zhang, Y. Wang. Four-coordinate organoboron compounds for organic light-emitting diodes (OLEDs)[J]. Chem. Soc. Rev., 2013,42:8416-8433. doi: 10.1039/c3cs60170f
16. [16]
  S.N. Wang. Luminescence and electroluminescence of Al(III), B(III), Be(II) and Zn(II) complexes with nitrogen donors[J]. Coord. Chem. Rev., 2001,215:79-98. doi: 10.1016/S0010-8545(00)00403-3
17. [17]
  L.S. Hung, C.H. Chen. Recent progress of molecular organic electroluminescent materials and devices[J]. Mater. Sci. Eng. R, 2002,39:143-222. doi: 10.1016/S0927-796X(02)00093-1
18. [18]
  L. Wang, K. Wang, B. Zou. Luminescent chromism of boron diketonate crystals: distinct responses to different stresses[J]. Adv. Mater., 2015,27:2918-2922. doi: 10.1002/adma.v27.18
19. [19]
  L. Wang, K. Wang, H.Y. Zhang. The facile realization of RGB luminescence based on one yellow emissive four-coordinate organoboron material[J]. Chem. Commun., 2015,51:7701-7704. doi: 10.1039/C5CC01113B
20. [20]
  X.Q. Wang, Q.S. Liu, H. Yan. Piezochromic luminescence behaviors of two new benzothiazole-enamido boron difluoride complexes: intra- and inter-molecular effects induced by hydrostatic compression[J]. Chem. Commun., 2015,51:7497-7500. doi: 10.1039/C5CC01902H
21. [21]
  H. Wang, F. Li, B.R. Gao. Doped organic crystals with high efficiency, colortunable emission toward laser application[J]. Cryst. Growth Des., 2009,9:4945-4950. doi: 10.1021/cg9007125
22. [22]
  S.J. Yoon, S.Y. Park. Polymorphic and mechanochromic luminescence modulation in the highly emissive dicyanodistyrylbenzene crystal: secondary bonding interaction in molecular stacking assembly[J]. J. Mater. Chem., 2011,21:8338-8346. doi: 10.1039/c0jm03711g
23. [23]
  M.S. Kwon, J. Gierschner, S.J. Yoon, S.Y. Park. Unique piezochromic fluorescence behavior of dicyanodistyrylbenzene based donor-acceptor-donor triad: mechanically controlled photo-induced electron transfer (eT) in molecular assemblies[J]. Adv. Mater., 2012,24:5487-5492. doi: 10.1002/adma.v24.40
24. [24]
  S.J. Yoon, J.W. Chung, J. Gierschner. Multistimuli two-color luminescence switching via different slip-stacking of highly fluorescent molecular sheets[J]. J. Am. Chem. Soc., 2010,132:13675-13683. doi: 10.1021/ja1044665
25. [25]
  C.F. Feng, K. Wang, Y.X. Xu. Unique piezochromic fluorescence behavior of organic crystal of carbazole-substituted CNDSB[J]. Chem. Commun., 2016,52:3836-3839. doi: 10.1039/C5CC09152G
26. [26]
  Y.X. Xu, K. Wang, Y.J. Zhang. Fluorescence mutation and structural evolution of a p-conjugated molecular crystal during phase transition[J]. J. Mater. Chem. C, 2016,4:1257-1262. doi: 10.1039/C5TC03745J
27. [27]
  H.J. Lee, J. Sohn, J. Hwang. Triphenylamine-cored bifunctional organic molecules for two-photon absorption and photorefraction[J]. Chem. Mater., 2004,16:456-465. doi: 10.1021/cm0343756
28. [28]
  Z.Y. Ge, T. Hayakawa, S. Ando. Spin-coated highly efficient phosphorescent organic light-emitting diodes based on bipolar triphenylamine-benzimidazole derivatives[J]. Adv. Funct. Mater., 2008,18:584-590. doi: 10.1002/(ISSN)1616-3028
29. [29]
  J.X. Wu, H.L. Wang, S.P. Xu, W.Q. Xu. Comparison of shearing force and hydrostatic pressure on molecular structures of triphenylamine by fluorescence and Raman spectroscopies[J]. J. Phys. Chem. A, 2015,119:1303-1308. doi: 10.1021/jp511380a
30. [30]
  Y.J. Zhang, K. Wang, G.L. Zhuang. Multicolored-fluorescence switching of ICT-type organic solids with clear color difference: mechanically controlled excited state[J]. Chem. Eur. J., 2015,21:2474-2479. doi: 10.1002/chem.v21.6
31. [31]
  J.B. Zhang, J.L. Chen, B. Xu. Remarkable fluorescence change based on the protonation-deprotonation control in organic crystals[J]. Chem. Commun., 2013,49:3878-3880. doi: 10.1039/c3cc41171k
32. [32]
  Y.J. Dong, B. Xu, J.B. Zhang. Supramolecular interactions induced fluorescent organic nanowires with high quantum yield based on 9,10-distyrylanthracene[J]. CrystEngComm, 2012,14:6593-6598. doi: 10.1039/c2ce25276g
33. [33]
  Y.J. Dong, B. Xu, J.B. Zhang. Piezochromic luminescence based on the molecular aggregation of 9,10-Bis((E)-2-(pyrid-2-yl)vinyl) anthracene[J]. Angew. Chem. Int. Ed., 2012,51:10782-10785. doi: 10.1002/anie.v51.43
34. [34]
  Y.J. Dong, J.B. Zhang, X. Tan. Multi-stimuli responsive fluorescence switching: the reversible piezochromism and protonation effect of a divinylanthracene derivative[J]. J. Mater. Chem. C, 2013,1:7554-7559. doi: 10.1039/c3tc31553c
35. [35]
  J.D. Luo, Z.L. Xie, J.W.Y. Lam, et al., Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole, Chem. Commun. (2001) 1740-1741.
36. [36]
  X.L. Luo, W.J. Zhao, J.Q. Shi. Reversible switching emissions of tetraphenylethene derivatives among multiple colors with solvent vapor, mechanical, and thermal stimuli[J]. J. Phys. Chem. C, 2012,116:21967-21972. doi: 10.1021/jp306908u
37. [37]
  N. Zhao, Z.Y. Yang, J.W.Y. Lam. Benzothiazolium-functionalized tetraphenylethene: an AIE luminogen with tunable solid-state emission[J]. Chem. Commun., 2012,48:8637-8639. doi: 10.1039/c2cc33780k
38. [38]
  J. Wang, J. Mei, R.R. Hu. Click synthesis, aggregation-induced emission, E/Z isomerization,self-organization,andmultiplechromismsofpurestereoisomersof a tetraphenylethene-cored luminogen[J]. J. Am. Chem. Soc., 2012,134:9956-9966. doi: 10.1021/ja208883h
39. [39]
  Q.K. Qi, J.Y. Qian, X. Tan. Remarkable turn-on and color-tuned piezochromic luminescence: mechanically switching intramolecular charge transfer in molecular crystals[J]. Adv. Funct. Mater., 2015,25:4005-4010. doi: 10.1002/adfm.v25.26
40. [40]
  H.S. Yuan, K. Wang, K. Yang, B.B. Liu, B. Zou. Luminescence properties of compressed tetraphenylethene: the role of intermolecular interactions[J]. J. Phys. Chem. Lett., 2014,5:2968-2973. doi: 10.1021/jz501371k
41. [41]
  J.X. Wu, J. Tang, H.L. Wang. Reversible piezofluorochromic property and intrinsic structure changes of tetra(4-methoxyphenyl)ethylene under high pressure[J]. J. Phys. Chem. A, 2015,119:9218-9224. doi: 10.1021/acs.jpca.5b02362
42. [42]
  K. Nagura, S. Saito, H. Yusa. Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chromism of tetrathiazolylthiophene[J]. J. Am. Chem. Soc., 2013,135:10322-10325. doi: 10.1021/ja4055228
43. [43]
  Y.J. Zhang, Q.B. Song, K. Wang. Polymorphic crystals and their luminescence switching of triphenylacrylonitrile derivatives upon solvent vapour, mechanical, and thermal stimuli[J]. J. Mater. Chem. C, 2015,3:3049-3054. doi: 10.1039/C4TC02826K
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