Preparation of 9,10-Diarylphenanthrene Derivative and Its Application in Full Color Emitters Synthesis

doi:10.1007/s40242-017-7044-7

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (4): 574-580.doi: 10.1007/s40242-017-7044-7

• Articles • Previous Articles Next Articles

Preparation of 9,10-Diarylphenanthrene Derivative and Its Application in Full Color Emitters Synthesis

ZHAO Wenkai¹, WANG Zhiming^1,3, LI Xueying¹, ZHANG Dongdong², ZHANG Xiaojuan¹, LU Ping²

1. School of Petrochemical Engineering, Shenyang University of Technology, Liaoyang 111003, P. R. China;
2. State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, P. R. China;
3. Shenzhen Research Institute, Hong Kong University of Science & Technology, Shenzhen 518057, P. R. China

Received:2017-02-07 Revised:2017-03-29 Online:2017-08-01 Published:2017-06-05
Contact: WANG Zhiming, LU Ping E-mail:wangzhm1983@163.com;lup@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China（No.51673118），the Natural Science Fund of Guangdong Province，China（No.2014A030313659） and the Science and Technology Plan of Shenzhen City，China（No.JCYC20160428150-429072）.

Abstract

Abstract:

As a building block with high photo-and thermo-stability, phenanthrene plays an important role in the preparation of blue(or deep-blue) and full color fluorescence materials. However, some critical issues must be addressed before its full potential can be realised, such as its tedious and low-yield modification processes and the red-shift effect in its aggregated state. In this work, the inexpensive raw material 9,10-phenanthrenequinone(PQ) was chosen as the preparatory functional phenanthrene block. After modifying PQ via halo-substituted, nucleophilic and rearrangement reactions with high yields, the corresponding monomers featured high reactivity and solubility. Compared with classical synthetic approaches for similar phenanthrene-based derivatives, the low efficiency ring-closed reaction and hazardous lithium-injection operation can be omitted using this approach. This new building block demonstrates a clear steric effect following the introduction of peripheral phenyl and alkoxy groups; moreover, stacking in the aggregated state is avoided, which benefits controlling the bandgap and maintaining blue emission as either an emitter or a donor. By changing the central building block in three oligomers, emission of the three primary colors was achieved in solution and film via the conjugated increment and charge-transform effect. This work provides a method of modifying phenanthrene by a simple and efficient synthesis route with inhibition of solid-state aggregation and offers an effective strategy to further develop functional phenanthrene-based building blocks.

Key words: Phenanthrene, Functionalization, Aggregation, Fluorescence, Three primary colors emission

ZHAO Wenkai, WANG Zhiming, LI Xueying, ZHANG Dongdong, ZHANG Xiaojuan, LU Ping. Preparation of 9,10-Diarylphenanthrene Derivative and Its Application in Full Color Emitters Synthesis[J]. Chemical Research in Chinese Universities, 2017, 33(4): 574-580.

References

[1] Wang C. L., Dong H. L., Hu W. P., Liu. Y. Q., Zhu D. B., Chem. Rev., 2012, 112(4), 2208
[2] Zhu M. R., Yang C. L., Chem. Soc. Rev., 2013, 42, 4963
[3] Murphy A. R., Fréchet J. M. J., Chem. Rev., 2007, 107(4), 1066
[4] Yao L., Yang B., Ma Y. G., Sci. China Chem., 2014, 57(3), 335
[5] Dong H. L., Zhu H. F., Meng Q., Gong X., Hu W. P., Chem. Soc. Rev., 2012, 41, 1754
[6] Ranger M., Rondeau D., Leclerc M., Macromolecules, 1997, 30(25), 7686
[7] Redecker M., Bradley D. D. C., Inbasekaran M., Wu W. W., Woo E. P., Adv. Funct. Mater., 1999, 11(3), 241
[8] Zeng G., Yu W. L., Chua S. J., Huang W., Macromolecules, 2002, 35(18), 6907
[9] Liu L. L., Tang S., Liu M. R., Xie Z. Q., Zhang W., Lu P., Hanif M., Ma Y. G., J. Phys. Chem. B, 2006, 110(28), 13734
[10] Park S. H., Jin Y., Kim J. Y., Kim S. H., Kim J., Suh H., Lee K., Adv. Funct. Mater., 2007, 17, 3063
[11] Kawano S., Yang C., Ribas M., Baumgarten M., Macromolecules, 2008, 41(21), 7933
[12] He B., Tian H. K., Geng Y. H., Wang F. S., Mullen K., Org. Lett., 2008, 10(5), 773
[13] Jordi P., Ruud V., Miquel S., J. Org. Chem., 2007, 72, 1134
[14] Boden B. N., Jardine K. J., Leung A. C. W., MacLachlan M. J., Org.Lett., 2006, 8(9), 1855
[15] Tang S., Li W. J., Shen F. Z., Liu D. D., Yang B., Ma Y. G., J. Mater. Chem., 2012, 22, 4401
[16] Liang H. J., Wang X. X., Zhang X. Y., Liu Z. Y., Ge Z. Y., Ouyang X. H., Wang S. D., New J. Chem., 2014, 38, 4696
[17] Tian H. K., Wang J., Shi J. W., Yan D. H., Wang L. X., Geng Y. H., Wang F. S., J. Mater. Chem., 2005, 15, 3026
[18] Grisorio R., Suranna G. P., Mastrorilli P., Nobile C. F., Org. Lett., 2007, 9(16), 3149
[19] Wang Z. M., Lu P., Chen S. M., Gao Z., Shen F. Z., Zhang W. S., Xu Y. X., Kwok H. S., Ma Y. G., J. Mater. Chem., 2011, 21, 5451
[20] Wang Z. M., Song X. H, Ma L. L., Feng Y., Gu C., Zhang X. J., Lu P., Ma Y. G., New J. Chem., 2013, 37, 2440
[21] Muddasir H., Lu P., Li M., Zheng Y., Xie Z. Q., Ma Y. G., Li D., Li J. H., Polym. Int., 2007, 56, 1507
[22] Grisorio R., Suranna G. P., Mastrorilli P., Nobile C. F., Org. Lett., 2007, 9, 3149
[23] Wang Z. M., Lu P., Xue S. F., Gu C., Lv Y., Zhu Q., Wang H., Ma Y. G., Dyes and Pigments, 2011, 91, 356
[24] Wang Z. M., Li X. Y., Xue K., Li H., Zhang X. J., Liu Y., Yu Z. Q., Lu P., Chen P., J. Mater. Chem. C, 2016, 4, 1886
[25] Zhang M., Xue S. F., Dong W. Y., Wang Q., Fei T., Gu C., Ma Y. G., Chem. Commun., 2010, 46, 3923
[26] Zou L. Y., Guan S. Li L. J., Zhao L., Chem. Res. Chinese Universities, 2015, 31(5), 801
[27] Yao C. F., Zeng H. P., Chem. Res. Chinese Universities, 2011, 27(4), 599
[28] Wang Z. M., Feng Y, Zhang S. T., Gao Y., Gao Z., Chen Y. M., Zhang X. J., Lu P., Yang B., Chen P., Ma Y. G., Liu S. Y., Phys. Chem. Chem. Phys., 2014, 16, 20772

Preparation of 9,10-Diarylphenanthrene Derivative and Its Application in Full Color Emitters Synthesis

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	WANG Yue, WANG Jinling, MA Jianxin, ZHANG Yue, XU Na, WANG Xiuli. Multi-functional Photoelectric Sensor Based on a Three-fold Interpenetrated Cd(II) Coordination Polymer for Sensitively Detecting Different Ions [J]. Chemical Research in Chinese Universities, 2022, 38(4): 1105-1110.
[2]	CHEN Zhangwu and LI Fen. Proton-induced Conversion from Non-Aufbau to Aufbau Electronic Structure of an Organic Radical with Turn-on Fluorescence [J]. Chemical Research in Chinese Universities, 2022, 38(3): 798-802.
[3]	XU Kai, HUANG Ning. Recent Advances of Covalent Organic Frameworks in Chemical Sensing [J]. Chemical Research in Chinese Universities, 2022, 38(2): 339-349.
[4]	NIU Junfeng, SUN Haiya, XIA Housheng, ZHU Yinbang, CHEN Jialing, ZHU Chengye, BAI Wei. Visualization of Bulk Polymerization by Fluorescent Probe with Aggregation-induced Emission Characteristics [J]. Chemical Research in Chinese Universities, 2022, 38(2): 500-504.
[5]	LI Mingfeng, FANG Hongbao, JI Yifan, CHEN Yuncong, HE Weijiang, GUO Zijian. Rational Design of Ratiometric Fe³⁺ Fluorescent Probes Based on FRET Mechanism [J]. Chemical Research in Chinese Universities, 2022, 38(1): 67-74.
[6]	LIU Xinyu, YAN Ye, ZHANG Qiang, ZHAO Kefeng, HAN Yanchun. n-Type D-A Conjugated Polymers: Relationship Between Microstructure and Electrical/Mechanical Performance [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1019-1030.
[7]	LU Feng, ZHAO Ting, SUN Xiaojun, WANG Zuqiang, FAN Quli, HUANG Wei. Rare-earth Doped Nanoparticles with Narrow NIR-II Emission for Optical Imaging with Reduced Autofluorescence [J]. Chemical Research in Chinese Universities, 2021, 37(4): 943-950.
[8]	YUAN Fang, LI Yang, CHEN Zhenjuan, ZHANG Jianjian, NING Lulu, YANG Xiao-Feng, PU Kanyi. Excimer-based Activatable Fluorescent Sensor for Sensitive Detection of Alkaline Phosphatase [J]. Chemical Research in Chinese Universities, 2021, 37(4): 960-966.
[9]	CHU Binbin, WANG Houyu, HE Yao. Fluorescent Silicon-based Nanomaterials Imaging Technology in Diseases [J]. Chemical Research in Chinese Universities, 2021, 37(4): 880-888.
[10]	YANG Yujie, YANG Jie, FANG Manman, LI Zhen. Recent Process of Photo-responsive Materials with Aggregation-induced Emission [J]. Chemical Research in Chinese Universities, 2021, 37(3): 598-614.
[11]	ZHENG Gaofeng, PENG Hao, JIANG Jiaxin, KANG Guoyi, LIU Juan, ZHENG Jianyi, LIU Yifang. Surface Functionalization of PEO Nanofibers Using a TiO₂ Suspension as Sheath Fluid in a Modified Coaxial Electrospinning Process [J]. Chemical Research in Chinese Universities, 2021, 37(3): 571-577.
[12]	YANG Liming, GUO Lixin, YU Hao, WANG Guan, SUN Jiangman, ZHANG Pengfei, GU Xinggui, TANG Ben Zhong. Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging [J]. Chemical Research in Chinese Universities, 2021, 37(1): 129-136.
[13]	PAN Quan, MA Feiyan, PU Xinqing, ZHAO Manyi, WU Qiling, ZHAO Na, YANG Jun, TANG Ben Zhong. A Novel Fluorescent Probe for ATP Detection Based on Synergetic Effect of Aggregation-induced Emission and Counterion Displacement [J]. Chemical Research in Chinese Universities, 2021, 37(1): 166-170.
[14]	HU Qinyu, WU Jun, CHEN Lulu, LOU Xiaoding, XIA Fan. Recent Development of DNA-modified AIEgen Probes for Biomedical Application [J]. Chemical Research in Chinese Universities, 2021, 37(1): 66-72.
[15]	FANG Fang, GAO Yuting, LUO Liang. Mitochondrion-anchoring AIEgen with Large Stokes Shift for Imaging-guided Photodynamic Therapy [J]. Chemical Research in Chinese Universities, 2021, 37(1): 137-142.