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

a  Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
b  Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
,
c  Department of Materials Science and Engineering, University of Toronto, Toronto, Canada
,
d  Chair of Inorganic Molecular Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
a  Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
› Institutsangaben
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.


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.

Supporting Information

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


Supplementary Material



Publikationsverlauf

Eingereicht: 25. März 2020

Angenommen: 13. Juni 2020

Publikationsdatum:
30. September 2020 (online)

© 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/).

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References and Notes

    • 1a Wu Y, Zhu W. Chem. Soc. Rev. 2013; 42: 2039
    • 1b Zhang J, Xu W, Sheng P, Zhao G, Zhu D. Acc. Chem. Res. 2017; 50: 1654
    • 1c Zhang J, Jin J, Xu H, Zhang Q, Huang W. J. Mater. Chem. C Mater. Opt. Electron. Devices 2018; 6: 3485
    • 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
    • 1e Li Y, Liu J.-Y, Zhao Y.-D, Cao Y.-C. Mater. Today 2017; 20: 258
    • 1f Geng H, Zheng X, Shuai Z, Zhu L, Yi Y. Adv. Mater. 2015; 27: 1443
    • 1g Richter M, Fu Y, Dmitrieva E, Weigand JJ, Popov A, Berger R, Liu J, Feng X. ChemPlusChem 2019; 84: 613
    • 2a Cao X, Zhang D, Zhang S, Tao Y, Huang W. J. Mater. Chem. C Mater. Opt. Electron. Devices 2017; 5: 7699
    • 2b Ledwon P. Org. Electron. 2019; 75: 105422
    • 2c Tao Y, Yuan K, Chen T, Xu P, Li H, Chen R, Zheng C, Zhang L, Huang W. Adv. Mater. 2014; 26: 7931
    • 3a Hong Y, Lam JW. Y, Tang BZ. Chem. Commun. (Camb.) 2009; (29) 4332
    • 3b Hong Y, Lam JW. Y, Tang BZ. Chem. Soc. Rev. 2011; 40: 5361
    • 4a Li H, Li BS, Tang BZ. Chem. Asian J. 2019; 14: 674
    • 4b Wang H, Zhao E, Lam JW. Y, Tang BZ. Mater. Today 2015; 18: 365
    • 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
    • 5b Shen P, Zhuang Z, Zhao Z, Tang BZ. J. Mater. Chem. C Mater. Opt. Electron. Devices 2018; 6: 11835
    • 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
    • 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
    • 6b Zhang W, Zhang F, Tang R, Fu Y, Wang X, Zhuang X, He G, Feng X. Org. Lett. 2016; 18: 3618
    • 6c Zhang W, Fu Y, Qiang P, Hunger J, Bi S, Zhang W, Zhang F. Org. Biomol. Chem. 2017; 15: 7106
    • 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
    • 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
    • 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
    • 7a Dou C, Ding Z, Zhang Z, Xie Z, Liu J, Wang L. Angew. Chem. Int. Ed. 2015; 54: 3648
    • 7b Wang T, Dou C, Liu J, Wang L. Chemistry 2018; 24: 13043
    • 8a Grant DJ, Dixon DA. J. Phys. Chem. A 2006; 110: 12955
    • 8b Blanksby SJ, Ellison GB. Acc. Chem. Res. 2003; 36: 255
    • 9a Mukundam V, Sa S, Kumari A, Das R, Venkatasubbaiah K. J. Mater. Chem. C Mater. Opt. Electron. Devices 2019; 7: 12725
    • 9b Qiu F, Zhang F, Tang R, Fu Y, Wang X, Han S, Zhuang X, Feng X. Org. Lett. 2016; 18: 1398
    • 9c Morgan MM, Nazari M, Pickl T, Rautiainen JM, Tuononen HM, Piers WE, Welch GC, Gelfand BS. Chem. Commun. (Camb.) 2019; 55: 11095
    • 9d Pammer F, Schepper J, Glöckler J, Sun Y, Orthaber A. Dalton Trans. 2019; 48: 10298
  • 10 Uchida K, Kubo T. J. Synth. Org. Chem. Jpn. 2016; 74: 1069
  • 11 Ishida N, Narumi M, Murakami M. Helv. Chim. Acta 2012; 95: 2474
    • 12a Ren X, Zhang F, Luo H, Liao L, Song X, Chen W. Chem. Commun. (Camb.) 2020; 56: 2159
    • 12b Araneda JF, Piers WE, Heyne B, Parvez M, McDonald R. Angew. Chem. Int. Ed. 2011; 50: 12214
  • 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
  • 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
  • 15 Berski S, Latajka Z, Gordon AJ. New J. Chem. 2011; 35: 89
    • 16a Janiak C. J. Chem. Soc., Dalton Trans. 2000; 3885
    • 16b Hunter CA, Sanders JK. M. J. Am. Chem. Soc. 1990; 112: 5525
    • 16c Banerjee A, Saha A, Saha BK. Cryst. Growth Des. 2019; 19: 2245
  • 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
    • 18a Lin JH, Elangovan A, Ho TI. J. Org. Chem. 2005; 70: 7397
    • 18b Yang W, Zhu W, Zhou W, Liu H, Xu Y, Fan J. J. Fluoresc. 2012; 22: 1383
  • 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
    • 20a Mei J, Hong Y, Lam JW. Y, Qin A, Tang Y, Tang BZ. Adv. Mater. 2014; 26: 5429
    • 20b Mei J, Leung NL. C, Kwok RT. K, Lam JW. Y, Tang BZ. Chem. Rev. 2015; 115: 11718
  • 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