Download PDF
CC BY-NC-ND 4.0 · Organic Materials 2020; 02(01): 033-040
DOI: 10.1055/s-0040-1701249
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

Solid-State Fluorescence Enhancement of Bromine-Substituted Trans-Enaminone Derivatives

Hua Li 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
,
Haiyang Shu 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
,
Xin Wang 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
,
Xiaofu Wu 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
,
Hongkun Tian 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
,
Hui Tong 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
,
Lixiang Wang 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b   University of Science and Technology of China, Hefei 230026, China
› Author Affiliations Funding Information This work was financially supported by the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB12010200) and the National Natural Science Foundation of China (Grant Nos. 51833009, 21674111, 21574131, 51973211, and 21322403).
Further Information

Publication History

Received: 29 September 2019

Accepted after revision: 02 December 2019

Publication Date:
30 January 2020 (online)

   Permissions and Reprints All articles of this category


Abstract

Halogen bonding, as a kind of intermolecular interaction, has rarely been used to tune solid-state emission properties of luminescent materials, especially fluorescent materials. Herein, three trans-enaminone (TE) derivatives (nonbrominated TE, monobrominated BrTE, and tribrominated Br3TE) with aggregation-induced emission property have been designed and synthesized. Two types of BrTE crystals (BrTE-B and BrTE-G) with different fluorescence properties were obtained. It was observed that their solid-state fluorescence has been enhanced by the formation of halogen bonding. In particular, the crystal BrTE-G containing Br…π interactions exhibits a fluorescence quantum yield (9.6%) nearly sevenfold higher than BrTE-B, the crystal without halogen bonding (1.4%), and fivefold higher than the nonbrominated TE derivative (2.1%). By careful inspection of the single-crystal data and theoretical calculations, the high fluorescence quantum yield of BrTE-G appears to be due to halogen-bonding interactions as well as multiple stronger intermolecular interactions which may restrain molecular motions, leading to the reduced nonradiative decay rate and the enhanced radiative decay rate. Additionally, increasing the number of bromine substituents may further promote the radiative decay rate, explaining therefore the higher fluorescence quantum yield (12.5%) of Br3TE.

Key words

halogen bonding - solid-state emission - aggregation-induced emission - fluorescence - crystals - enaminones

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1701249.


Supporting Information

 

  • References

    • 1a Chen CT. Chem. Mater. 2004; 16: 4389
      CrossrefPubMed
    • 1b Ding D, Li K, Liu B, Tang BZ. Acc. Chem. Res. 2013; 46: 2441
      CrossrefPubMed
    • 1c Luo D, Xiao P, Liu B. Chem. Rec. 2019; 19: 1596
      CrossrefPubMed
    • 1d Sedgwick AC, Wu L, Han HH, Bull SD, He XP, James TD, Sessler JL, Tang BZ, Tian H, Yoon J. Chem. Soc. Rev. 2018; 47: 8842
      CrossrefPubMed
    • 2a Li Q, Li Z. Adv. Sci. 2017; 4: 1600484
      CrossrefPubMed
    • 2b Mei J, Leung NL, Kwok RT, Lam JW, Tang BZ. Chem. Rev. 2015; 115: 11718
      PubMed
    • 2c Naito H, Morisaki Y, Chujo Y. Angew. Chem. Int. Ed. 2015; 54: 5084
      CrossrefPubMed
  • 3 Luo J, Xie Z, Lam JW, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Chem. Commun. 2001; 1740
    PubMed
    • 4a Yuan WZ, Tan Y, Gong Y, Lu P, Lam JW, Shen XY, Feng C, Sung HH, Lu Y, Williams ID, Sun JZ, Zhang Y, Tang BZ. Adv. Mater. 2013; 25: 2837
      CrossrefPubMed
    • 4b Cai S, Shi H, Tian D, Ma H, Cheng Z, Wu Q, Gu M, Huang L, An Z, Peng Q, Huang W. Adv. Funct. Mater. 2018; 28: 1705045
      CrossrefPubMed
    • 5a Yu T, Ou D, Yang Z, Huang Q, Mao Z, Chen J, Zhang Y, Liu S, Xu J, Bryce MR, Chi Z. Chem. Sci. 2017; 8: 1163
      CrossrefPubMed
    • 5b Xia G, Jiang Z, Shen S, Liang K, Shao Q, Cong Z, Wang H. Adv. Opt. Mater. 2019; 7: 1801549
      CrossrefPubMed
  • 6 Sagara Y, Kato T. Angew. Chem. Int. Ed. 2008; 47: 5175
    CrossrefPubMed
  • 7 Song X, Zhang Z, Zhang S, Wei J, Ye K, Liu Y, Marder TB, Wang Y. J. Phys. Chem. Lett. 2017; 8: 3711
    CrossrefPubMed
    • 8a Xu B, Li W, He J, Wu S, Zhu Q, Yang Z, Wu YC, Zhang Y, Jin C, Lu PY, Chi Z, Liu S, Xu J, Bryce MR. Chem. Sci. 2016; 7: 5307
      CrossrefPubMed
    • 8b He Z, Zhang L, Mei J, Zhang T, Lam JW Y, Shuai Z, Dong YQ, Tang BZ. Chem. Mater. 2015; 27: 6601
      CrossrefPubMed
    • 8c Wu Q, Ma H, Ling K, Gan N, Cheng Z, Gu L, Cai S, An Z, Shi H, Huang W. ACS Appl. Mater. Interfaces 2018; 10: 33730
      CrossrefPubMed
    • 8d Zhang Y, Feng YQ, Tian XX, Wang JH, Li H, Han G, Li D. Adv. Opt. Mater. 2018; 6: 1800903
      CrossrefPubMed
    • 9a Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, Politzer P, Resnati G, Rissanen K. Pure. Appl. Chem. 2013; 85: 1711
      CrossrefPubMed
    • 9b Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G. Chem. Rev. 2016; 116: 2478
      CrossrefPubMed
  • 10 Wang C, Danovich D, Mo Y, Shaik S. J. Chem. Theory Comput. 2014; 10: 3726
    CrossrefPubMed
    • 11a Christopherson JC, Topić F, Barrett CJ, Friščić T. Cryst. Growth Des. 2018; 18: 1245
      CrossrefPubMed
    • 11b Tepper R, Schubert US. Angew. Chem. Int. Ed. 2018; 57: 6004
      CrossrefPubMed
    • 12a Bunchuay T, Docker A, Martinez-Martinez AJ, Beer PD. Angew. Chem. Int. Ed. 2019; 58: 13823
      CrossrefPubMed
    • 12b Gropp C, Husch T, Trapp N, Reiher M, Diederich F. J. Am. Chem. Soc. 2017; 139: 12190
      CrossrefPubMed
    • 12c Gropp C, Quigley BL, Diederich F. J. Am. Chem. Soc. 2018; 140: 2705
      CrossrefPubMed
  • 13 Bulfield D, Huber SM. Chem. Eur. J. 2016; 22: 14434
    CrossrefPubMed
    • 14a Ang SJ, Chwee TS, Wong MW. J. Phys. Chem. C. 2018; 122: 12441
      CrossrefPubMed
    • 14b Wang J, Wang C, Gong Y, Liao Q, Han M, Jiang T, Dang Q, Li Y, Li Q, Li Z. Angew. Chem. Int. Ed. 2018; 57: 16821
      CrossrefPubMed
    • 14c Kanosue K, Ando S. ACS Macro Lett. 2016; 5: 1301
      CrossrefPubMed
    • 15a Kenry, Chen C, Liu B. Nat. Commun. 2019; 10: 2111
      CrossrefPubMed
    • 15b Lucenti E, Forni A, Botta C, Giannini C, Malpicci D, Marinotto D, Previtali A, Righetto S, Cariati E. Chem. Eur. J. 2019; 25: 2452
      CrossrefPubMed
    • 15c Wang J, Wang C, Gong Y, Liao Q, Han M, Jiang T, Dang Q, Li Y, Li Q, Li Z. Angew. Chem. Int. Ed. 2018; 57: 16821
      CrossrefPubMed
    • 15d Bolton O, Lee K, Kim HJ, Lin KY, Kim J. Nat. Chem. 2011; 3: 205
      CrossrefPubMed
    • 16a Chen W, Zhang S, Dai G, Chen Y, Li M, Zhao X, Chen Y, Chen L. Chem. Eur. J. 2019; 25: 469
      PubMed
    • 16b D'Aléo A, Saul A, Attaccalite C, Fages F. Mater. Chem. Front. 2019; 3: 86
      CrossrefPubMed
    • 16c DeRosa CA, Kerr C, Fan Z, Kolpaczynska M, Mathew AS, Evans RE, Zhang G, Fraser CL. ACS Appl. Mater. Interfaces 2015; 7: 23633
      CrossrefPubMed
    • 16d Shi H, An Z, Li PZ, Yin J, Xing G, He T, Chen H, Wang J, Sun H, Huang W, Zhao Y. Cryst. Growth Des. 2016; 16: 808
      CrossrefPubMed
    • 16e Yan D, Delori A, Lloyd GO, Friscic T, Day GM, Jones W, Lu J, Wei M, Evans DG, Duan X. Angew. Chem. Int. Ed. 2011; 50: 12483
      CrossrefPubMed
    • 16f Salunke JK, Durandin NA, Ruoko TP, Candeias NR, Vivo P, Vuorimaa-Laukkanen E, Laaksonen T, Priimagi A. Sci. Rep. 2018; 8: 14431
      CrossrefPubMed
  • 17 Li H, Shu H, Liu Y, Wu X, Tian H, Tong H, Wang L. Adv. Opt. Mater. 2019; 7: 1801719
    CrossrefPubMed
    • 18a Chisholm DR, Valentine R, Pohl E, Whiting A. J. Org. Chem. 2016; 81: 7557
      CrossrefPubMed
    • 18b Chassaing S, Kueny-Stotz M, Isorez G, Brouillard R. Eur. J. Org. Chem. 2007; 15: 2438
      PubMed
    • 19a Sasaki S, Drummen GP. C, Konishi GI. J. Mater. Chem. C 2016; 4: 2731
      CrossrefPubMed
    • 19b Zbigniew R, Grabowski KR. Chem. Rev. 2003; 103: 3899
      CrossrefPubMed
  • 20 Isayama K, Aizawa N, Kim JY, Yasuda T. Angew. Chem. Int. Ed. 2018; 57: 11982
    CrossrefPubMed