Citation: Li Wen-Bo, Luo Wei-Jian, Li Kai-Xuan, Yuan Wang-Zhang, Zhang Yong-Ming. Aggregation-induced phosphorescence and mechanochromic luminescence of a tetraphenylethene-based gold(Ⅰ) isocyanide complex[J]. Chinese Chemical Letters, ;2017, 28(6): 1300-1305. doi: 10.1016/j.cclet.2017.04.008 shu

Aggregation-induced phosphorescence and mechanochromic luminescence of a tetraphenylethene-based gold(Ⅰ) isocyanide complex

Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Yuan Wang-Zhang, wzhyuan@sjtu.edu.cn Zhang Yong-Ming, ymzsjtu@gmail.com
Received Date: 4 January 2017
Revised Date: 21 February 2017
Accepted Date: 10 April 2017
Available Online: 17 June 2017

Figures(7)

In this study, a new twisting gold(Ⅰ) isocyanide complex based on tetraphenylethene (TPE), TPE-NC-Au, was designed and synthesized. It exhibits aggregation induced phosphorescence (AIP) characteristics, owing to the incorporation of Au moiety and conformation rigidification in the aggregated states. Moreover, the emission color of the crystalline solid of TPE-NC-Au changes from blue (454 nm) to green (500 nm) in response to mechanical grinding, due to the combined effects of conformation planarization, enhanced π…π stacking, as well as the emergence of aurophilic interactions in the ground amorphous state. Notably, the emission color can be restored upon solvent fuming, associating with the reconstruction of crystalline lattices. The AIP and switchable mechanochromism of TPE-NC-Au make it suitable for potential applications in bioimaging, sensing, and optoelectronic devices.
- Aggregation-induced phosphorescence,
- Mechanochromism,
- Aurophilic interaction,
- Gold(Ⅰ) isocyanide complex
1. [1]
  Li C.Y., Tang X., Zhang L.Q.. Reversible luminescence switching of an organic solid:controllable on-off persistent room temperature phosphorescence and stimulated multiple fluorescence conversion[J]. Adv. Opt. Mater., 2015,3:1184-1190. doi: 10.1002/adom.v3.9
2. [2]
  Zhang J.J., Zou Q., Tian H.. Photochromic materials:more than meets the eye[J]. Adv. Mater., 2013,25:378-399. doi: 10.1002/adma.201201521
3. [3]
  Mei J., Wang J., Qin A.J.. Construction of soft porous crystal with silole derivative:strategy of framework design, multiple structural transformability and mechanofluorochromism[J]. J. Mater. Chem., 2012,22:4290-4298. doi: 10.1039/C1JM12673C
4. [4]
  Dou C.D., Chen D., Iqbal J.. Multistimuli-responsive benzothiadiazolecored phenylene vinylene derivative with nanoassembly properties[J]. Langmuir, 2011,27:6323-6329. doi: 10.1021/la200382b
5. [5]
  Zhang G.Q., Lu J.W., Fraser C.L.. Mechanochromic luminescence quenching:force-enhanced singlet-to-triplet intersystem crossing for iodide-substituted difluoroboron-dibenzoylmethane-dodecane in the solid state[J]. Inorg. Chem., 2010,49:10747-10749. doi: 10.1021/ic902591s
6. [6]
  Luo J., Li L.Y., Song Y.L.. A piezochromic luminescent complex:mechanical force induced patterning with a high contrast ratio[J]. Chem. Eur. J., 2011,17:10515-10519. doi: 10.1002/chem.201101284
7. [7]
  Chi Z., Zhang X.Q., Xu B.J.. Recent advances in organic mechanofluorochromic materials[J]. Chem. Soc. Rev., 2012,41:3878-3896. doi: 10.1039/c2cs35016e
8. [8]
  Qi Q.K., Qian J.Y., Tan X.. 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
9. [9]
  Yuan W.Z., Tan Y.Q., Gong Y.Y.. Synergy between twisted conformation and effective intermolecular interactions:strategy for efficient mechanochromic luminogens with high contrast[J]. Adv. Mater., 2013,25:2837-2843. doi: 10.1002/adma.201205043
10. [10]
  Dong Y.J., Xu B., Zhang J.B.. Piezochromic luminescence based on the molecular aggregation of 9, 10-Bis ((E)-2-(pyrid-2-yl) vinyl) anthracene[J]. Angew. Chem., 2012,124:10940-10943. doi: 10.1002/ange.v124.43
11. [11]
  Ma Z.Y., Wang Z.J., Teng M.J.. Mechanically induced multicolor change of luminescent materials[J]. Chem. Phys. Chem., 2015,16:1811-1828. doi: 10.1002/cphc.v16.9
12. [12]
  Shi J.Q., Zhao W.J., Li C.H.. Switching emissions of two tetraphenylethene derivatives with solvent vapor, mechanical, and thermal stimuli[J]. Chin. Sci. Bull., 2013,58:2723-2727. doi: 10.1007/s11434-013-5868-1
13. [13]
  Wang Z.J., Ma Z.Y., Wang Y.. A novel mechanochromic and photochromic polymer film:when rhodamine joins polyurethane[J]. Adv. Mater., 2015,27:6469-6474. doi: 10.1002/adma.201503424
14. [14]
  Wang J., Mei J., Hu R.R.. Click synthesis, aggregation-induced emission, E/Z isomerization, self-organization, and multiple chromisms of pure stereoisomers of a tetraphenylethene-cored luminogen[J]. J. Am. Chem. Soc., 2012,134:9956-9966. doi: 10.1021/ja208883h
15. [15]
  Huang K.W., Wu H.Z., Shi M.. Reply to comment on 'aggregation-induced phosphorescent emission (AIPE) of iridium (Ⅲ) complexes':origin of the enhanced phosphorescence[J]. Chem. Commun., 2009:1243-1245.
16. [16]
  Ouyang M., Zhan L.L., Lv X.J.. Clear piezochromic behaviors of AIE-active organic powders under hydrostatic pressure[J]. RSC Adv., 2016,6:1188-1193. doi: 10.1039/C5RA21218A
17. [17]
  Yang J., Ren Z.C., Xie Z.L.. AIEgen with fluorescence-phosphorescence dual mechanoluminescence at room temperature[J]. Angew. Chem., 2017. doi: 10.1002/ange.201610453
18. [18]
  Wang L., Ye K.Q., Zhang H.Y.. Organic materials with hydrostatic pressure induced mechanochromic properties[J]. Chin. Chem. Lett., 2016,27:1367-1375. doi: 10.1016/j.cclet.2016.06.049
19. [19]
  Han J.Q., Sun J.Y., Li Y.P.. One-pot synthesis of a mechanochromic AIE luminogen:implication for rewritable optical data storage[J]. J. Mater. Chem. C., 2016,4:9287-9293. doi: 10.1039/C6TC03131E
20. [20]
  Xu B.J., Li W.L., He J.J.. Achieving very bright mechanoluminescence from purely organic luminophores with aggregation-induced emission by crystal design[J]. Chem. Sci., 2016,7:5307-5312. doi: 10.1039/C6SC01325B
21. [21]
  Shi C.X., Guo Z.Q., Yan Y.L.. Self-assembly solid-state enhanced red emission of quinolinemalononitrile:optical waveguides and stimuli response[J]. ACS Appl. Mat. Interfaces., 2012,5:192-198.
22. [22]
  Xie T.Q., Zhang B.C., Zhang X.P.. AIE-active β-diketones containing pyridiniums:fluorogenic binding to cellulose and water-vapour-recoverable mechanochromic luminescence[J]. Mater. Chem. Front., 2017,1:693-696. doi: 10.1039/C6QM00187D
23. [23]
  Shan G.G., Li H.B., Qin J.S.. Piezochromic luminescent (PCL) behavior and aggregation-induced emission (AIE) property of a new cationic iridium (Ⅲ) complex[J]. Dalton Trans., 2012,41:9590-9593. doi: 10.1039/c2dt31013a
24. [24]
  Luo X.L., Li J.N., Li C.H.. Reversible switching of the emission of diphenyldibenzofulvenes by thermal and mechanical stimuli[J]. Adv. Mater., 2011,23:3261-3265. doi: 10.1002/adma.201101059
25. [25]
  Zhang X.Q., Chi Z.G., Zhang Y.. Recent advances in mechanochromic luminescent metal complexes[J]. J. Mater. Chem. C., 2013,1:3376-3390. doi: 10.1039/c3tc30316k
26. [26]
  Zhang X., Wang J.Y., Ni J.. Vapochromic and mechanochromic phosphorescence materials based on a platinus(Ⅱ) complex with trifluoromethylacetylide[J]. Inorg. Chem., 2012,51:5569-5579. doi: 10.1021/ic202421d
27. [27]
  King K.A., Spellane P.J., Watts R.J.. Excited-state properties of a triply orthometalated iridium(Ⅲ) complex[J]. J. Am. Chem. Soc., 1985,107:1431-1432. doi: 10.1021/ja00291a064
28. [28]
  Kawamura Y., Goushi K., Brooks J.. 100% phosphorescence quantum efficiency of Ir(Ⅲ) complexes in organic semiconductor films[J]. Appl. Phys. Lett., 2005,86071104. doi: 10.1063/1.1862777
29. [29]
  Rodríguez L., Ferrer M., Crehuet R.. Correlation between photophysical parameters and gold-gold distances in gold(Ⅰ) (4-pyridyl) ethynyl complexes[J]. Inorg. Chem., 2012,51:7636-7641. doi: 10.1021/ic300609f
30. [30]
  Seki T., Sakurada K., Muromoto M.. Photoinduced single-crystal-tosingle-crystal phase transition and photosalient effect of a gold(Ⅰ) isocyanide complex with shortening of intermolecular aurophilic bonds[J]. Chem. Sci., 2015,6:1491-1497. doi: 10.1039/C4SC02676D
31. [31]
  Ito H., Saito T., Oshima N.. Reversible mechanochromic luminescence of[(C6F5Au)2(m-1, 4-diisocyanobenzene)[J]. J. Am. Chem. Soc., 2008,130:10044-10045. doi: 10.1021/ja8019356
32. [32]
  Liang J.H., Chen Z., Yin J.. Aggregation-induced emission (AIE) behavior and thermochromic luminescence properties of a new gold(Ⅰ) complex[J]. Chem. Commun., 2013,49:3567-3569. doi: 10.1039/c3cc00157a
33. [33]
  Seki T., Ozaki T., Okura T.. Interconsertible multiple photoluminescence color of a gold(Ⅰ) isocyanide complex in the solid state:solvent-induced blueshifted and mechano-responsive red-shifted photoluminescence[J]. Chem. Sci., 2015,6:2187-2195. doi: 10.1039/C4SC03960B
34. [34]
  Zhao Z.J., Lam J.W.Y., Tang B.Z.. Tetraphenylethene:a versatile AIE building block for the construction of efficient luminescent materials for organic lightemitting diodes[J]. J. Mater. Chem., 2012,22:23723-23740.
35. [35]
  Wang F., Li X., Wang S.. New π-conjugated cyanostilbene derivatives:synthesis, characterization and aggregation-induced emission[J]. Chin. Chem. Lett., 2016,27:1592-1596. doi: 10.1016/j.cclet.2016.04.020
36. [36]
  Dong Y.Q., Lam J.W.Y., Qin A.J.. Aggregation-induced emissions of tetraphenylethene derivatives and their utilities as chemical vapor sensors and in organic light-emitting diodes[J]. Appl. Phys. Lett., 2007,91011111. doi: 10.1063/1.2753723
37. [37]
  Duan X.F., Zeng J., Lü J.W.. Insights into the general and efficient cross McMurry reactions between ketones[J]. Org. Chem., 2006,71:9873-9876. doi: 10.1021/jo061644d
38. [38]
  Leifert D., Daniliuc C.G., Studer A.. 6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS)[J]. Org. Lett., 2013,15:6286-6289. doi: 10.1021/ol403147v
39. [39]
  Seki T., Takamatsu Y., Ito H.. A screening approach for the discovery of mechanochromic gold(Ⅰ) isocyanide complexes with crystal-to-crystal phase transitions[J]. J. Am. Chem. Soc., 2016,138:6252-6260. doi: 10.1021/jacs.6b02409
40. [40]
  Kawaguchi K., Seki T., Karatsu T.. Cholesterol-aided construction of distinct self-organized materials from a luminescent gold(Ⅰ)-isocyanide complex exhibiting mechanochromic luminescence[J]. Chem. Commun., 2013,49:11391-11393. doi: 10.1039/c3cc47162d
41. [41]
  Szytuła A., Fus D., Penc B.. Electronic structure of RTX (R=Pr, Nd; T=Cu, Ag, Au; X=Ge, Sn) compounds[J]. J. Alloys Compd., 2001,317:340-346.
42. [42]
  Uson R., Laguna A., Laguna M.. Inorg[J]. Synth., 2007,26:85-91.
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