Citation: Wang Yunzhong, He Zihan, Chen Gan, Shan Tong, Yuan Wangzhang, Lu Ping, Zhang Yongming. D-A structured high efficiency solid luminogens with tunable emissions: Molecular design and photophysical properties[J]. Chinese Chemical Letters, ;2017, 28(11): 2133-2138. doi: 10.1016/j.cclet.2017.09.054 shu

D-A structured high efficiency solid luminogens with tunable emissions: Molecular design and photophysical properties

Wang Yunzhong ^a,1 ,
He Zihan ^a,1 ,
Chen Gan ^a ,
Shan Tong ^b ,
Yuan Wangzhang ^a,, ,
Lu Ping ^b,, ,
Zhang Yongming ^a,,

a.
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, Shanghai Jiao Tong University, Shanghai 200240, China
b.
State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, China

Corresponding author: Yuan Wangzhang, wzhyuan@sjtu.edu.cn Lu Ping, lup@jlu.edu.cn Zhang Yongming, ymzsjtu@gmail.com

Received Date: 4 July 2017
Revised Date: 21 September 2017
Accepted Date: 21 September 2017
Available Online: 28 November 2017

Figures(4)

Fabrication of efficient solid luminogens with tunable emission is both fundamentally significant and technically important. Herein, based on our previous strategy for the construction of efficient and multifunctional solid luminogens through the combination of diverse aggregation-induced emission (AIE) units with other functional moieties, a group of luminophores with electron donor-acceptor (D-A) structure and typical intramolecular charge transfer (ICT) characteristics, namely CZ-DCDPP, DPA-DCDPP and DBPA-DCDPP were synthesized and investigated. The presence of twisting and AIE-active 2, 3-dicyano-5, 6-diphenylpyrazine (DCDPP) moiety endows them highly emissive in the solid states, whereas the introduction of arylamines with varied electron-donating capacity and different conjugation render them with tunable solid emissions from green to red. While CZ-DCDPP and DPA-DCDPP solids exhibit distinct mechanochromism, both DPA-DCDPP and DBPA-DCDPP solids can generate efficient red emission. Owing to their high efficiency, remarkable thermal and morphological stabilities and moreover red emission, they are promising for diverse optoelectronic and biological applications.
- Aggregation-induced emission,
- Intramolecular charge transfer,
- Electron donor-acceptor,
- Efficient solid luminogens,
- Luminescence mechanochromism,
- Red emission
1. [1]
  L. Yao, S. Zhang, R. Wang, et al., Angew. Chem. Int. Ed. 53(2014) 2119-2123. doi: 10.1002/anie.201308486
2. [2]
  S. Wang, X. Yan, Z. Cheng, et al., Angew. Chem. Int. Ed. 54(2015) 13068-13072. doi: 10.1002/anie.v54.44
3. [3]
  W.C. Chen, Y. Yuan, S.F. Ni, et al., Chem. Sci. 8(2017) 3599-3608. doi: 10.1039/C6SC05619A
4. [4]
  Y.J. Luo, Z.Y. Lu, Y. Huang, Chin. Chem. Lett. 27(2016) 1223-1230. doi: 10.1016/j.cclet.2016.06.002
5. [5]
  M. Fang, J. Huang, Y. Zhang, et al., Mater. Chem. Front. 1(2017) 668-676. doi: 10.1039/C6QM00133E
6. [6]
  D. Ding, K. Li, B. Liu, B.Z. Tang, Acc. Chem. Res. 46(2013) 2441-2453. doi: 10.1021/ar3003464
7. [7]
  M. Wang, G. Zhang, D. Zhang, D. Zhu, B.Z. Tang, J. Mater. Chem. 20(2010) 1858-1867. doi: 10.1039/b921610c
8. [8]
  C. Ge, Y. Liu, X. Ye, et al., Mater. Chem. Front. 1(2017) 530-537. doi: 10.1039/C6QM00146G
9. [9]
  H. Lu, Y. Zheng, X. Zhao, et al., Angew. Chem. Int. Ed. 55(2016) 155-159. doi: 10.1002/anie.201507031
10. [10]
  Q. Wan, R. Jiang, L. Mao, et al., Mater. Chem. Front. 1(2017) 1051-1058. doi: 10.1039/C6QM00307A
11. [11]
  J. Qian, Z. Zhu, C.W.T. Leung, et al., Biomed. Opt. Express 6(2015) 1477-1486. doi: 10.1364/BOE.6.001477
12. [12]
  Y. Kubota, J. Uehara, K. Funabiki, M. Ebihara, M. Matsui, Tetrahedron Lett. 51(2010) 6195-6198. doi: 10.1016/j.tetlet.2010.09.106
13. [13]
  J. Luo, Z. Xie, J.W.Y. Lam, et al., Chem. Commun. 381(2001) 1740-1741.
14. [14]
  W.Z. Yuan, Y. Tan, Y. Gong, et al., Adv. Mater. 25(2013) 2837-2843. doi: 10.1002/adma.201205043
15. [15]
  J. Mei, N.L.C. Leung, et al., Chem. Rev. 115(2015) 11718-11940. doi: 10.1021/acs.chemrev.5b00263
16. [16]
  M. Chen, L. Li, H. Nie, et al., Chem. Sci. 6(2015) 1932-1937. doi: 10.1039/C4SC03365E
17. [17]
  P.C. Shen, Z.Y. Zhuang, Z.J. Zhao, B.Z. Tang, Chin. Chem. Lett. 27(2016) 1115-1123. doi: 10.1016/j.cclet.2016.06.031
18. [18]
  S. Xu, T. Liu, Y. Mu, et al., Angew. Chem. Int. Ed. 54(2015) 874-878. doi: 10.1002/anie.201409767
19. [19]
  Z. Wang, B. Xu, L. Zhang, et al., Nanoscale 5(2013) 2065-2072. doi: 10.1039/c2nr33685e
20. [20]
  Y. Dong, J.W.Y. Lam, A. Qin, J. Sun, H.S. Kwok, et al., Appl. Phys. Lett. 91(2007) 011111. doi: 10.1063/1.2753723
21. [21]
  T. Han, X. Feng, B. Tong, et al., Chem. Commun. 48(2012) 416-418. doi: 10.1039/C1CC15681K
22. [22]
  W.Z. Yuan, P. Lu, S. Chen, et al., Adv. Mater. 22(2010) 2159-2163. doi: 10.1002/adma.v22:19
23. [23]
  Y. Liu, S. Chen, J.W.Y. Lam, et al., Chem. Mater. 23(2011) 2536-2544. doi: 10.1021/cm2003269
24. [24]
  W.Z. Yuan, S. Chen, J.W.Y. Lam, et al., Chem. Commun. 47(2011) 11216-11218. doi: 10.1039/c1cc14122h
25. [25]
  W.Z. Yuan, Y. Gong, S. Chen, et al., Chem. Mater. 24(2012) 1518-1528. doi: 10.1021/cm300416y
26. [26]
  Z. Yang, Z. Chi, T. Yu, et al., J. Mater. Chem. 19(2009) 5541-5546. doi: 10.1039/b902802a
27. [27]
  G. Chen, W. Li, T. Zhou, et al., Adv. Mater. 27(2015) 4496-4501. doi: 10.1002/adma.v27.30
28. [28]
  R. Hu, E. Lager, A. Aguilar-Aguilar, et al., J. Phys. Chem. C 113(2009) 15845-15853. doi: 10.1021/jp902962h
29. [29]
  Y.W. Lu, Y.Q. Tan, Y.Y. Gong, et al., Chin. Sci. Bull. 58(2013) 2719-2722. doi: 10.1007/s11434-013-5893-0
30. [30]
  A. Qin, J.W.Y. Lam, F. Mahtab, et al., Appl. Phys. Lett. 94(2009) 2007-2010.
31. [31]
  B. Gao, Q. Zhou, Y. Geng, et al., Mater. Chem. Phys. 99(2006) 247-252. doi: 10.1016/j.matchemphys.2005.10.020
32. [32]
  X. Zhang, M. Liu, B. Yang, et al., Polym. Chem. 4(2013) 5060-5064. doi: 10.1039/c3py00860f
33. [33]
  Q. Zhao, K. Li, S. Chen, et al., J. Mater. Chem. 22(2012) 15128-15135. doi: 10.1039/c2jm31368e
34. [34]
  X. Han, Q. Bai, L. Yao, et al., Adv. Funct. Mater. 25(2015) 7521-7529. doi: 10.1002/adfm.v25.48
35. [35]
  The emission maxima of the compounds in DMF are difficult to be accurately identified even after signal amplification, owing to their rather low intensities.
36. [36]
  Z. Chi, X. Zhang, B. Xu, et al., Chem. Soc. Rev. 41(2012) 3878-3896. doi: 10.1039/c2cs35016e
37. [37]
  W.B. Li, W.J. Luo, K.X. Li, W.Z. Yuan, Y.M. Zhang, Chin.Chem. Lett. 28(2017) 1300-1305. doi: 10.1016/j.cclet.2017.04.008
38. [38]
  Z. Ma, Z. Wang, X. Meng, et al., Angew. Chem. Int. Ed. 55(2016) 519-522. doi: 10.1002/anie.201507197
39. [39]
  Y. Gong, Y. Tan, J. Liu, et al., Chem. Commun. 49(2013) 4009-4011. doi: 10.1039/c3cc39243k
40. [40]
  X.Y. Teng, X.C. Wu, Y.Q. Cao, et al., Chin. Chem. Lett. 28(2017), doi:http://dx.doi.org/10.1016/j.cclet.2017.02.018. doi: 10.1016/j.cclet.2017.02.018
41. [41]
  C. Hang, H.W. Wu, L.L. Zhu, Chin. Chem. Lett. 27(2016) 1155-1165. doi: 10.1016/j.cclet.2016.04.003
42. [42]
  S.L. Tao, Z.K. Peng, X.H. Zhang, et al., Adv. Funct. Mater. 15(2005) 1716-1721. doi: 10.1002/(ISSN)1616-3028
43. [43]
  J. Huang, N. Sun, Y. Dong, et al., Adv. Funct. Mater. 23(2013) 2329-2337. doi: 10.1002/adfm.201202639
44. [44]
  No glass transition was observed for CZ-DCDPP during the measurement.
45. [45]
  ITO. =indium tinoxide, HATCN=1, 4, 5, 8, 9, 11-hexaazatriphenylene hexacarbonitrile (HATCN), NPB=N, N' -bis(naphthalen-1-yl)-N, N' -bis(phenyl) benzidine, TCTA=tris(4-carbazoyl-9-ylphenyl)amine, TPBi=1, 3, 5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, CBP=4, 4'-bis(9-carbazolyl)-2, 2'-biphenyl.
46. [46]
  L. Xu, Y. Zhao, G. Long, et al., RSC Adv. 5(2015) 63080-63086. doi: 10.1039/C5RA12654A
1. [1]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
2. [2]
  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
3. [3]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
4. [4]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
5. [5]
  Rui Cheng , Xin Huang , Tingting Zhang , Jiazhuang Guo , Jian Yu , Su Chen . Solid superacid catalysts promote high-performance carbon dots with narrow-band fluorescence emission for luminescence solar concentrators. Chinese Chemical Letters, 2024, 35(8): 109278-. doi: 10.1016/j.cclet.2023.109278
6. [6]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
7. [7]
  Jiayuan Liang , Xin Mi , Songhao Guo , Hui Luo , Kejun Bu , Tonghuan Fu , Menglin Duan , Yang Wang , Qingyang Hu , Rengen Xiong , Peng Qin , Fuqiang Huang , Xujie Lü . Pressure-induced emission in 0D metal halide (EATMP)SbBr5 by regulating exciton-phonon coupling. Chinese Journal of Structural Chemistry, 2024, 43(7): 100333-100333. doi: 10.1016/j.cjsc.2024.100333
8. [8]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
9. [9]
  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
10. [10]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
11. [11]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
12. [12]
  Bohan Zhang , Bingzhe Wang , Guichuan Xing , Zikang Tang , Songnan Qu . Regulation of the multi-emission centers in carbon dots via a bottom-up synthesis approach. Chinese Chemical Letters, 2024, 35(9): 109358-. doi: 10.1016/j.cclet.2023.109358
13. [13]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
14. [14]
  Chun-Yun Ding , Ru-Yuan Zhang , Yu-Wu Zhong , Jiannian Yao . Binary and heterostructured microplates of iridium and ruthenium complexes: Preparation, characterization, and thermo-responsive emission. Chinese Journal of Structural Chemistry, 2024, 43(10): 100393-100393. doi: 10.1016/j.cjsc.2023.100393
15. [15]
  Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
16. [16]
  Ting WANG , Peipei ZHANG , Shuqin LIU , Ruihong WANG , Jianjun ZHANG . A Bi-CP-based solid-state thin-film sensor: Preparation and luminescence sensing for bioamine vapors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1615-1621. doi: 10.11862/CJIC.20240134
17. [17]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
18. [18]
  Lei Wang , Jun-Jie Wu , Chang-Cun Yan , Wan-Ying Yang , Zong-Lu Che , Xin-Yu Xia , Xue-Dong Wang , Liang-Sheng Liao . Near-infrared organic lasers with ultra-broad emission bands by simultaneously harnessing four-level and six-level systems. Chinese Chemical Letters, 2024, 35(8): 109365-. doi: 10.1016/j.cclet.2023.109365
19. [19]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
20. [20]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(593)
HTML views(37)

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