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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 240-247
DOI: 10.1055/s-0040-1715564
Short Communication

Synthesis and Characterization of AIE-Active B–N-Coordinated Phenalene Complexes

Yubin Fu 
a   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
Junzhi Liu 
b   Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
,
Zhongbin Wu 
c   Department of Materials Science and Engineering, University of Toronto, Toronto, Canada
,
Jan J. Weigand 
d   Chair of Inorganic Molecular Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
Xinliang Feng 
a   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
› Author Affiliations Funding Information We thank the European Union's Horizon 2020 research and innovation program under grant agreement No. 696656 (Graphene Flagship Core2), ERC Grant on T2DCP, the German Research Foundation (DFG) within the Cluster of Excellence “Center for Advancing Electronics Dresden (cfaed)” and EnhanceNano (No. 391979941) as well as the European Social Fund and the Federal State of Saxony (ESF Project “GRAPHD”, TU Dresden) for financial support. J. Liu is grateful for the startup funding from The University of Hong Kong and the funding support from ITC to the SKL.
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Abstract

Organoboron compounds provide a new line to tune the electronic structures of π-conjugated molecules, which is critical to the development of new organic semiconductor materials. In this work, we demonstrate the synthesis of two novel boron–nitrogen (B−N) coordinated phenalene complexes (BNP-PX and BNP-PA) by employing BN phenalene (BNP) as the acceptor unit and phenoxazine/phenylphenazine groups as the donors. Based on single-crystal X-ray analysis, both BNP-PX and BNP-PA possess highly twisted conformations with the dihedral angles of 76.6 ° and 70.5 °, respectively. The photophysical properties of BNP-PX and BNP-PA are elucidated through UV-vis absorption, fluorescence spectroscopy, and theoretical calculations. In addition, BNP-PX exhibits a large Stokes shift (8,033 cm−1) and excellent aggregated-induced emission behavior. The red organic light-emitting diode device was fabricated based on compound BNP-PX, manifesting its promising application in organic optoelectronic devices.

Key words

donor–acceptor - BN-coordinated compounds - large Stokes shift - AIE effect - OLED device

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1715564.


Supplementary Material



Publication History

Received: 25 March 2020

Accepted: 13 June 2020

Article published online:
30 September 2020

© 2020. 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/).

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

    • 1a Wu Y, Zhu W. Chem. Soc. Rev. 2013; 42: 2039
      CrossrefPubMed
    • 1b Zhang J, Xu W, Sheng P, Zhao G, Zhu D. Acc. Chem. Res. 2017; 50: 1654
      CrossrefPubMed
    • 1c Zhang J, Jin J, Xu H, Zhang Q, Huang W. J. Mater. Chem. C Mater. Opt. Electron. Devices 2018; 6: 3485
      CrossrefPubMed
    • 1d Zhang G, Zhao J, Chow PC. Y, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem. Rev. 2018; 118: 3447
      CrossrefPubMed
    • 1e Li Y, Liu J.-Y, Zhao Y.-D, Cao Y.-C. Mater. Today 2017; 20: 258
      CrossrefPubMed
    • 1f Geng H, Zheng X, Shuai Z, Zhu L, Yi Y. Adv. Mater. 2015; 27: 1443
      CrossrefPubMed
    • 1g Richter M, Fu Y, Dmitrieva E, Weigand JJ, Popov A, Berger R, Liu J, Feng X. ChemPlusChem 2019; 84: 613
      CrossrefPubMed
    • 2a Cao X, Zhang D, Zhang S, Tao Y, Huang W. J. Mater. Chem. C Mater. Opt. Electron. Devices 2017; 5: 7699
      CrossrefPubMed
    • 2b Ledwon P. Org. Electron. 2019; 75: 105422
      CrossrefPubMed
    • 2c Tao Y, Yuan K, Chen T, Xu P, Li H, Chen R, Zheng C, Zhang L, Huang W. Adv. Mater. 2014; 26: 7931
      CrossrefPubMed
    • 3a Hong Y, Lam JW. Y, Tang BZ. Chem. Commun. (Camb.) 2009; (29) 4332
      PubMed
    • 3b Hong Y, Lam JW. Y, Tang BZ. Chem. Soc. Rev. 2011; 40: 5361
      CrossrefPubMed
    • 4a Li H, Li BS, Tang BZ. Chem. Asian J. 2019; 14: 674
      CrossrefPubMed
    • 4b Wang H, Zhao E, Lam JW. Y, Tang BZ. Mater. Today 2015; 18: 365
      CrossrefPubMed
    • 5a Fu Y, Qiu F, Zhang F, Mai Y, Wang Y, Fu S, Tang R, Zhuang X, Feng X. Chem. Commun. (Camb.) 2015; 51: 5298
      CrossrefPubMed
    • 5b Shen P, Zhuang Z, Zhao Z, Tang BZ. J. Mater. Chem. C Mater. Opt. Electron. Devices 2018; 6: 11835
      CrossrefPubMed
    • 5c Wan W.-M, Tian D, Jing Y.-N, Zhang X.-Y, Wu W, Ren H, Bao H.-L. Angew. Chem. Int. Ed. 2018; 57: 15510
      CrossrefPubMed
    • 6a Wang X, Zhang F, Liu J, Tang R, Fu Y, Wu D, Xu Q, Zhuang X, He G, Feng X. Org. Lett. 2013; 15: 5714
      CrossrefPubMed
    • 6b Zhang W, Zhang F, Tang R, Fu Y, Wang X, Zhuang X, He G, Feng X. Org. Lett. 2016; 18: 3618
      CrossrefPubMed
    • 6c Zhang W, Fu Y, Qiang P, Hunger J, Bi S, Zhang W, Zhang F. Org. Biomol. Chem. 2017; 15: 7106
      CrossrefPubMed
    • 6d Wang X, Zhang F, Gao J, Fu Y, Zhao W, Tang R, Zhang W, Zhuang X, Feng X. J. Org. Chem. 2015; 80: 10127
      CrossrefPubMed
    • 6e Wang X, Zhang F, Schellhammer KS, Machata P, Ortmann F, Cuniberti G, Fu Y, Hunger J, Tang R, Popov AA, Berger R, Müllen K, Feng X. J. Am. Chem. Soc. 2016; 138: 11606
      CrossrefPubMed
    • 6f Fu Y, Zhang K, Dmitrieva E, Liu F, Ma J, Weigand JJ, Popov AA, Berger R, Pisula W, Liu J, Feng X. Org. Lett. 2019; 21: 1354
      CrossrefPubMed
    • 7a Dou C, Ding Z, Zhang Z, Xie Z, Liu J, Wang L. Angew. Chem. Int. Ed. 2015; 54: 3648
      CrossrefPubMed
    • 7b Wang T, Dou C, Liu J, Wang L. Chemistry 2018; 24: 13043
      CrossrefPubMed
    • 9a Mukundam V, Sa S, Kumari A, Das R, Venkatasubbaiah K. J. Mater. Chem. C Mater. Opt. Electron. Devices 2019; 7: 12725
      CrossrefPubMed
    • 9b Qiu F, Zhang F, Tang R, Fu Y, Wang X, Han S, Zhuang X, Feng X. Org. Lett. 2016; 18: 1398
      CrossrefPubMed
    • 9c Morgan MM, Nazari M, Pickl T, Rautiainen JM, Tuononen HM, Piers WE, Welch GC, Gelfand BS. Chem. Commun. (Camb.) 2019; 55: 11095
      CrossrefPubMed
    • 9d Pammer F, Schepper J, Glöckler J, Sun Y, Orthaber A. Dalton Trans. 2019; 48: 10298
      CrossrefPubMed
  • 10 Uchida K, Kubo T. J. Synth. Org. Chem. Jpn. 2016; 74: 1069
    CrossrefPubMed
  • 11 Ishida N, Narumi M, Murakami M. Helv. Chim. Acta 2012; 95: 2474
    CrossrefPubMed
    • 12a Ren X, Zhang F, Luo H, Liao L, Song X, Chen W. Chem. Commun. (Camb.) 2020; 56: 2159
      CrossrefPubMed
    • 12b Araneda JF, Piers WE, Heyne B, Parvez M, McDonald R. Angew. Chem. Int. Ed. 2011; 50: 12214
      CrossrefPubMed
  • 13 Synthetic procedure for compound BNP-PX: In a 50 mL one-necked flask, compound 8 (153.5 mg, 0.32 mmol), alkynylborate (120.9 mg, 0.35 mmol), DPEPhos (16.3 mg, 0.03 mmol) and Pd(π-allyl)Cl (17.2 mg, 0.047 mmol) were charged under argon atmosphere. After three times vacuum-argon operation, degassed toluene (10 mL) was added into the flask under argon. Then the mixture was stirred at 60 °C for 12 h. Afterwards, the reaction mixture was concentrated under reduced pressure. The residue was then purified by chromatography on silica gel (CH2Cl2/iso-hexane = 1/1) to give product as red powder (167.8 mg, 91%). 1H NMR (300 MHz, CD2Cl2) δ 8.87 (dd, J = 5.5, 1.5 Hz, 1H), 8.67 (dd, J = 8.4, 1.5 Hz, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 7.7 Hz, 1H), 7.47 (dd, J = 8.4, 5.5 Hz, 1H), 7.38 (d, J = 1.5 Hz, 2H), 7.35 (d, J = 1.3 Hz, 2H), 7.24 (s, 1H), 7.21 (t, J = 1.7 Hz, 1H), 7.18 (d, J = 1.5 Hz, 2H), 7.16 (s, 2H), 7.14 (dd, J = 3.2, 1.5 Hz, 2H), 7.12 (s, 3H), 7.10 (dd, J = 4.1, 2.1 Hz, 1H), 6.78 (dd, J = 7.9, 1.6 Hz, 2H), 6.71 (td, J = 7.6, 1.4 Hz, 2H), 6.58 (td, J = 7.7, 1.6 Hz, 2H), 5.86 (d, J = 1.4 Hz, 1H), 5.84 (d, J = 1.4 Hz, 1H). 11B NMR (96 MHz, CD2Cl2) δ 2.20. 13C NMR (76 MHz, CD2Cl2) δ 153.6, 150.8, 146.1, 144.3, 140.5, 137.4, 134.8, 134.5, 134.2, 133.0, 132.5, 131.2, 128.5, 128.3, 127.8, 127.7, 126.7, 125.8, 125.2, 124.0, 122.6, 122.5, 116.1, 113.8. HRMS (ACPI, m/z): calcd for C41H30BN2O+ [M + H]+ 577.2451, found 577.2447
    PubMed
  • 14 Synthetic procedure for compound BNP-PA: In a 50 mL one-necked flask, compound 9 (59.9 mg, 0.11 mmol), alkynylborate (49.8 mg, 0.14 mmol), DPEPhos (13.0 mg, 0.024 mmol) and Pd(π-allyl)Cl (14.4 mg, 0.039 mmol) were charged under argon atmosphere. After three times vacuum-argon operation, degassed toluene (5 mL) was added into the flask under argon. Then the mixture was stirred at 60 °C for 12 h. After cooling down to room temperature, anhydrous methanol (15 mL) was added into the flask and some brown solid precipitated to the bottom. The solid was collected by filtration and then washed by MeOH. The dark brown to black solid (43.0 mg, 60%) can be used directly for further characterization. 1H NMR (300 MHz, CD2Cl2) δ 8.96 (dd, J = 8.4, 1.6 Hz, 1H), 8.92–8.84 (m, 1H), 7.94 (d, J = 7.7 Hz, 1H), 7.85 (d, J = 7.7 Hz, 1H), 7.68 (t, J = 7.6 Hz, 3H), 7.60–7.51 (m, 2H), 7.46 (d, J = 7.7 Hz, 3H), 7.38 (d, J = 1.7 Hz, 2H), 7.35 (s, 2H), 7.25–7.17 (m, 4H), 7.15 (d, J = 5.9 Hz, 3H), 7.12 (d, J = 2.7 Hz, 5H), 6.30 (t, J = 7.5 Hz, 2H), 6.21 (t, J = 7.5 Hz, 2H), 5.71–5.64 (m, 2H), 5.57–5.49 (m, 2H). 11B NMR (96 MHz, CD2Cl2) δ –5.37. 13C NMR (76 MHz, CD2Cl2) δ 150.8, 146.2, 140.9, 140.3, 137.8, 137.0, 136.4, 134.5, 134.5, 134.0, 133.5, 131.8, 131.6, 131.5, 129.3, 128.8, 128.6, 128.3, 127.7, 127.6, 126.6, 125.8, 125.3, 122.5, 121.9, 121.3, 113.2, 112.9. HRMS (ACPI, m/z): calcd for C47H34BN3 + [M]+ 651.2846, found 651.2845
    PubMed
  • 15 Berski S, Latajka Z, Gordon AJ. New J. Chem. 2011; 35: 89
    CrossrefPubMed
    • 16a Janiak C. J. Chem. Soc., Dalton Trans. 2000; 3885
      PubMed
    • 16b Hunter CA, Sanders JK. M. J. Am. Chem. Soc. 1990; 112: 5525
      CrossrefPubMed
    • 16c Banerjee A, Saha A, Saha BK. Cryst. Growth Des. 2019; 19: 2245
      CrossrefPubMed
  • 17 Sun L, Zhang F, Wang X, Qiu F, Xue M, Tregnago G, Cacialli F, Osella S, Beljonne D, Feng X. Chem. Asian J. 2015; 10: 709
    CrossrefPubMed
    • 18a Lin JH, Elangovan A, Ho TI. J. Org. Chem. 2005; 70: 7397
      CrossrefPubMed
    • 18b Yang W, Zhu W, Zhou W, Liu H, Xu Y, Fan J. J. Fluoresc. 2012; 22: 1383
      CrossrefPubMed
  • 19 Anandhan K, Cerón M, Perumal V, Ceballos P, Gordillo-Guerra P, Pérez-Gutiérrez E, Castillo AE, Thamotharan S, Percino MJ. RSC Advances 2019; 9: 12085
    CrossrefPubMed
    • 20a Mei J, Hong Y, Lam JW. Y, Qin A, Tang Y, Tang BZ. Adv. Mater. 2014; 26: 5429
      CrossrefPubMed
    • 20b Mei J, Leung NL. C, Kwok RT. K, Lam JW. Y, Tang BZ. Chem. Rev. 2015; 115: 11718
      CrossrefPubMed
  • 21 Kong Y.-J, Yan Z.-P, Li S, Su H.-F, Li K, Zheng Y.-X, Zang S.-Q. Angew. Chem. Int. Ed. 2020; 59: 5336
    CrossrefPubMed