logo

SCIENCE CHINA Chemistry, Volume 62 , Issue 10 : 1393-1397(2019) https://doi.org/10.1007/s11426-019-9576-7

Conformational sensitivity of tetraphenyl-1,3-butadiene derivatives with aggregation-induced emission characteristics

More info
  • ReceivedMay 27, 2018
  • AcceptedAug 5, 2019
  • PublishedAug 29, 2019

Abstract


Funded by

the National Natural Science Foundation of China(51673024,21875019,21490574,51803009)

Beijing Institute of Technology Research Fund Program for Young Scholars.


Acknowledgment

This work was supported by the National Natural Science Foundation of China (51673024, 21875019, 21490574, 51803009) and Beijing Institute of Technology Research Fund Program for Young Scholars.


Interest statement

The authors declare that they have no conflict of interest.


Supplement

Supporting information

The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.


References

[1] Luo J, Xie Z, Lam JWY, Cheng L, Tang BZ, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D. Chem Commun, 2001, : 1740-1741 CrossRef Google Scholar

[2] Chen Y, Lam JWY, Kwok RTK, Liu B, Tang BZ. Mater Horiz, 2019, 6: 428-433 CrossRef Google Scholar

[3] Zhang Y, Mao H, Xu W, Shi J, Cai Z, Tong B, Dong Y. Chem Eur J, 2018, 24: 15965-15977 CrossRef PubMed Google Scholar

[4] Wang H, Zhao E, Lam JWY, Tang BZ. Mater Today, 2015, 18: 365-377 CrossRef Google Scholar

[5] Zhao Z, He B, Tang BZ. Chem Sci, 2015, 6: 5347-5365 CrossRef PubMed Google Scholar

[6] Nie H, Chen B, Zeng J, Xiong Y, Zhao Z, Tang BZ. J Mater Chem C, 2018, 6: 3690-3698 CrossRef Google Scholar

[7] Nie H, Chen B, Quan C, Zhou J, Qiu H, Hu R, Su SJ, Qin A, Zhao Z, Tang BZ. Chem Eur J, 2015, 21: 8137-8147 CrossRef PubMed Google Scholar

[8] Yan X, Wang H, Hauke CE, Cook TR, Wang M, Saha ML, Zhou Z, Zhang M, Li X, Huang F, Stang PJ. J Am Chem Soc, 2015, 137: 15276-15286 CrossRef PubMed Google Scholar

[9] Tian G, Sun D, Zhang Y, Yu X. Angew Chem Int Ed, 2019, 58: 5951-5955 CrossRef PubMed Google Scholar

[10] Guan W, Zhou W, Lu C, Tang BZ. Angew Chem Int Ed, 2015, 54: 15160-15164 CrossRef PubMed Google Scholar

[11] Yan X, Wang M, Cook TR, Zhang M, Saha ML, Zhou Z, Li X, Huang F, Stang PJ. J Am Chem Soc, 2016, 138: 4580-4588 CrossRef PubMed Google Scholar

[12] Dai D, Li Z, Yang J, Wang C, Wu JR, Wang Y, Zhang D, Yang YW. J Am Chem Soc, 2019, 141: 4756-4763 CrossRef PubMed Google Scholar

[13] Zhang Y, Kong L, Shi J, Tong B, Zhi J, Feng X, Dong Y. Chin J Chem, 2015, 33: 701-704 CrossRef Google Scholar

[14] Zhang Y, Kong L, Mao H, Pan X, Shi J, Tong B, Dong Y. Mater Chem Front, 2017, 1: 2569-2573 CrossRef Google Scholar

[15] Zhang Y, Kong L, Pan X, Mao H, Zeng X, Shi J, Tong B, Dong Y. Dyes Pigments, 2017, 139: 714-719 CrossRef Google Scholar

[16] Zhang Y, Mao H, Kong L, Tian Y, Tian Z, Zeng X, Zhi J, Shi J, Tong B, Dong Y. Dyes Pigments, 2016, 133: 354-362 CrossRef Google Scholar

[17] Zhang Y, Xu W, Kong L, Han B, Cai Z, Shi J, Tong B, Dong Y, Tang B. Mater Chem Front, 2018, 2: 1779-1783 CrossRef Google Scholar

[18] Lei Y, Liu Q, Dong L, Cai Z, Shi J, Zhi J, Tong B, Dong Y. Chem Eur J, 2018, 24: 14269-14274 CrossRef PubMed Google Scholar

[19] Gao Y, Feng G, Jiang T, Goh C, Ng L, Liu B, Li B, Yang L, Hua J, Tian H. Adv Funct Mater, 2015, 25: 2857-2866 CrossRef Google Scholar

[20] Li K, Liu Y, Li Y, Feng Q, Hou H, Tang BZ. Chem Sci, 2017, 8: 7258-7267 CrossRef PubMed Google Scholar

[21] Li Y, Lei Y, Dong L, Zhang L, Zhi J, Shi J, Tong B, Dong Y. Chem Eur J, 2019, 25: 573–581. Google Scholar

[22] Wang Y, Mao PD, Wu WN, Mao XJ, Fan YC, Zhao XL, Xu ZQ, Xu ZH. Sens Actuat B-Chem, 2018, 255: 3085-3092 CrossRef Google Scholar

[23] Ding S, Liu M, Hong Y. Sci China Chem, 2018, 61: 882-891 CrossRef Google Scholar

[24] Kwok RTK, Leung CWT, Lam JWY, Tang BZ. Chem Soc Rev, 2015, 44: 4228-4238 CrossRef PubMed Google Scholar

[25] Yan L, Zhang Y, Xu B, Tian W. Nanoscale, 2016, 8: 2471-2487 CrossRef PubMed ADS Google Scholar

[26] Zhang X, Wang K, Liu M, Zhang X, Tao L, Chen Y, Wei Y. Nanoscale, 2015, 7: 11486-11508 CrossRef PubMed ADS Google Scholar

[27] Bai Y, Liu D, Han Z, Chen Y, Chen Z, Jiao Y, He W, Guo Z. Sci China Chem, 2018, 61: 1413-1422 CrossRef Google Scholar

[28] Song Y, Zong L, Zhang L, Li Z. Sci China Chem, 2017, 60: 1596-1601 CrossRef Google Scholar

[29] Liu T, Zhu L, Zhong C, Xie G, Gong S, Fang J, Ma D, Yang C. Adv Funct Mater, 2017, 27: 1606384 CrossRef Google Scholar

[30] Song F, Xu Z, Zhang Q, Zhao Z, Zhang H, Zhao W, Qiu Z, Qi C, Zhang H, Sung HHY, Williams ID, Lam JWY, Zhao Z, Qin A, Ma D, Tang BZ. Adv Funct Mater, 2018, 28: 1800051 CrossRef Google Scholar

[31] Chen S, Zeng P, Wang W, Wang X, Wu Y, Lin P, Peng Z. J Mater Chem C, 2019, 7: 2886-2897 CrossRef Google Scholar

[32] Kokubo K, Matsumasa K, Miura M, Nomura M. J Org Chem, 1996, 61: 6941-6946 CrossRef PubMed Google Scholar

[33] Shibata K, Satoh T, Miura M. Adv Synth Catal, 2007, 349: 2317-2325 CrossRef Google Scholar

[34] Vaz PAAM, Rocha J, Silva AMS, Guieu S. New J Chem, 2016, 40: 8198-8201 CrossRef Google Scholar

[35] Wang Q, Schlenoff JB. Macromolecules, 2014, 47: 3108-3116 CrossRef ADS Google Scholar

[36] Fares HM, Wang Q, Yang M, Schlenoff JB. Macromolecules, 2019, 52: 610-619 CrossRef ADS Google Scholar

[37] Yang M, Shi J, Schlenoff JB. Macromolecules, 2019, 52: 1930-1941 CrossRef ADS Google Scholar

[38] Fares HM, Ghoussoub YE, Delgado JD, Fu J, Urban VS, Schlenoff JB. Macromolecules, 2018, 51: 4945-4955 CrossRef ADS Google Scholar

[39] Fares HM, Schlenoff JB. J Am Chem Soc, 2017, 139: 14656-14667 CrossRef PubMed Google Scholar

  • Scheme 1

    Synthetic route to TPBs (color online).

  • Figure 1

    (a) Correlation between the net change in PL intensity [(II0)/I0] and (b) the maximum emission wavelengths (λmax) of TPBs with different water fractions in the THF/water mixtures. I0: the maximum PL intensity in THF; I: the maximum PL intensity in a mixture of THF/water; [TPB-1]=[TPB-2]=[TPB-3]=1×10−5 mol/L; excitation wavelength: 330 nm (color online).

  • Figure 2

    ORTEP drawing of the molecular conformation of (a) TPB-1, (b) TPB-2 and (c) TPB-3 in their single crystal (deletion of hydrogen atoms for clarity); intermolecular interactions of (d) TPB-1, (e) TPB-2 and (f) TPB-3 (color online).

  • Figure 3

    The PL intensity ratio of PEC-TPB at 470 and 390 nm (I470/I390) with different concentrations of KBr at 0.1%, 0.15% and 0.2% TPB-3 in PEC (color online).