Synthesis, Crystal Structure and Spectroscopic Properties of Two Fluorene-based Derivatives

ZHAO Ya-yun; LIU Zhi-peng; ZHAO Xiu-hua; ZHANG Jie; LI Xing

doi:10.3788/fgxb20143502.0156

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Synthesis, Crystal Structure and Spectroscopic Properties of Two Fluorene-based Derivatives

更新时间：2020-08-12

- Synthesis, Crystal Structure and Spectroscopic Properties of Two Fluorene-based Derivatives
- Chinese Journal of Luminescence Vol. 35, Issue 2, Pages: 156-164(2014)
- 作者机构：
  
  1. 宁波大学材料科学与化学工程学院,浙江宁波,315211
  2. 湘潭大学化学学院,湖南湘潭,411105
  3. 宁波大学理学院,浙江宁波,315211
- 作者简介：
- 基金信息：
  
  Sponsored by K. C. Wong Magna Fund in Ningbo University
- DOI：10.3788/fgxb20143502.0156
  CLC： TN383+.1;O625.15+3
- Received：23 August 2013，
  
  Revised：11 October 2013，
  
  Published：03 February 2014
- 稿件说明：
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赵亚云, 刘志鹏, 赵秀华等. 两种新型芴衍生物的合成、晶体结构及光谱性能[J]. 发光学报, 2014,35(2): 156-164

ZHAO Ya-yun, LIU Zhi-peng, ZHAO Xiu-hua etc. Synthesis, Crystal Structure and Spectroscopic Properties of Two Fluorene-based Derivatives[J]. Chinese Journal of Luminescence, 2014,35(2): 156-164
赵亚云, 刘志鹏, 赵秀华等. 两种新型芴衍生物的合成、晶体结构及光谱性能[J]. 发光学报, 2014,35(2): 156-164 DOI： 10.3788/fgxb20143502.0156.

ZHAO Ya-yun, LIU Zhi-peng, ZHAO Xiu-hua etc. Synthesis, Crystal Structure and Spectroscopic Properties of Two Fluorene-based Derivatives[J]. Chinese Journal of Luminescence, 2014,35(2): 156-164 DOI： 10.3788/fgxb20143502.0156.

摘要

合成了两种新型芴衍生物:2，7-二（3，5-二（三氟甲基）苯基）-9，9-二乙基芴（1）和2，7-二（4-氟苯基）-9，9-二乙基芴（2）。通过元素分析、红外光谱（IR）、核磁共振氢谱（

H NMR）以及单晶X射线衍射对其结构进行了表征。化合物1属于单斜晶系，

空间群;化合物2属于三斜晶系，

-1空间群。通过紫外-可见吸收和荧光光谱研究了化合物的发光性能。结果表明:在CH

溶液和固态薄膜中，化合物1、2在350～400 nm波段有吸收峰，归属于-

电荷跃迁;化合物1、2的光学带隙

分别为3.31 eV和3.30 eV，并且均有强烈的蓝色荧光发射现象（激发波长为330 nm），在二氯甲烷中的荧光量子效率分别为0.62和0.61，固态荧光寿命分别为6.39 ns和9.00 ns。

Abstract

Two new types of fluorene derivatives

7-bis(3

5-bis(trifluoromethyl)phenyl)-9

9-diethyl fluorene (C

=646.51

compound 1) and 2

7-bis(4-fluorophenyl)-9

9-diethyl fluorene (C

=410.48

compound 2) were synthesized and characterized by elemental analysis

IR spectra and single-crystal X-ray diffraction. Compound 1 belonged to monoclinic crystal system

space group

P21/c

and compound 2 was of triclinic with space group

-1. Their optoelectric properties were measured by UV-Vis absorption spectra and fluorescence spectra. The results show that compound 1 and 2 have low-energy absorption bands ranging from 350 nm to 400 nm in dichloromethane solution or solid film

which can be assigned to the -

charge transfer transitions. The optical band gaps (

) of 1 and 2 are estimated to be 3.31 eV and 3.30 eV

respectively. The title compounds exhibite strong blue photoluminescence under 330 nm excitation at room temperature. The fluorescence quantum yields in CH

of compound 1 and 2 are 0.62 and 0.61

and solid-state lifetimes are 6.39 ns and 9.00 ns

respectively.

关键词

Keywords

references

Knauer K A, Najafabadi E, Haske W, et al. Stacked inverted top-emitting green electrophosphorescent organic light-emitting diodes on glass and flexible glass substrates [J]. Org. Electron., 2013, 14(10):2418-2423. [2] Wang J, Wan W, Jiang H Z, et al. C-9 fluorenyl substituted anthracenes: A promising new family of blue luminescent materials [J]. Org. Lett., 2010, 12(17):3874-3877. [3] Reineke S, Lindner F, Schwartz G, et al. White organic light-emitting diodes with fluorescent tube efficiency [J]. Nature, 2009, 459:234-239. [4] Lo S C, Burn P L. Development of dendrimers: Macromolecules for use in organic light-emitting diodes and solar cells [J]. Chem. Rev., 2007, 107(4):1097-1116. [5] Xiang N J, Li D H, Liang W L, et al. Synthesis and photoluminescence of two novel bipolar organic compounds [J]. Acta Chim. Sinica (化学学报), 2006, 64(11):1157-1162 (in Chinese). [6] Prachumrak N, Thangthong A M, Tarsang R, et al. Synthesis, characterization, physical properties, and applications of highly fluorescent pyrene-functionalized 9,9-bis(4-diarylaminophenyl)fluorene in organic light-emitting diodes [J]. Tetrahedron Lett., 2012, 53:5492-5496. [7] Peng Z K, Tao S L, Zhang X H, et al. New fluorene derivatives for blue electroluminescent devices:Influence of substituents on thermal properties, photoluminescence, and electroluminescence [J]. J. Phys. Chem. C, 2008, 112(6):2165-2169. [8] Yu Z B, Wang M L, Lei G T, et al. Stabilizing the dynamic p-i-n junction in polymer light-emitting electrochemical cells [J]. J. Phys. Chem. Lett., 2011, 2(5):367-372. [9] Han L Z, Wang Z, Hua Y J, et al. Optoelectronic properties of 9,9-bis-(3-(9-phenyl-carbazoyl))- 2,7-dipyrenylfluorene [J]. Acta Chim. Sinica (化学学报), 2012, 70(5):579-584 (in Chinese). [10] Ye S H, Chen J M, Di C A, et al. Phenyl-substituted fluorene-dimer cored anthracene derivatives: Highly fluorescent and stable materials for high performance organic blue- and white-light-emitting diodes [J]. J. Mater. Chem., 2010, 20:3186-3194. [11] Thangthong A M, Prachumrak N, Tarsang R, et al. Blue light-emitting and hole-transporting materials based on 9,9-bis(4-diphenylaminophenyl)fluorenes for efficient electroluminescent devices [J]. J. Mater. Chem., 2012, 22:6869-6877. [12] Lin Y, Chen Y, Ye T L, et al. Carbazole-modified blue light-emitting copolymers with the backbones integrated by diphenyloxadiazole, fluorene, and triphenylamine [J]. Eur. Polym. J., 2012, 48:416-424. [13] Kaisa E L, Himadri S M, Fredrik S P, et al. Enhanced performance of printed organic diodes using a thin interfacial barrier layer [J]. Appl. Mater. Interf., 2011, 3(1):7-10. [14] Kulkarni A P, Zhu Y, Jenekhe S A. Quinoxaline-containing polyfluorenes: Synthesis, photophysics, and stable blue electroluminescene [J]. Macromolecules, 2005, 38(4):1553-1563. [15] Yang W, Huang J, Liu C, et al. Enhancement of color purity in blue-emitting fluorene-pyridine-based copolymers by controlling the chain rigidity and effective conjugation length [J]. Polymer, 2004, 45:865-872. [16] Zhan X, Liu Y, Wu X, et al. New series of blue-emitting and electron-transporting copolymers based on fluorine [J]. Macromolecules, 2002, 35(7):2529-2537. [17] Shimizu M, Hiyama T. Modem synthetic methods for fluorine-substituted target molecules [J]. Angew. Chem. Int. Ed., 2005, 44(2):214-231. [18] Sakamoto Y, Suzuki T, Tokito S, et al. Perfluoropentacene: H-performance p-n junctions and complementary circuits with pentacene [J]. J. Am. Chem. Soc., 2004, 126(26):8138-8140. [19] Kannan R, He G S, Yuan L X, et al. Diphenylaminofluorene-based two-photon-absorbing chromophores with various -electron acceptors [J]. Chem. Mater., 2001, 13(5):1896-1904. [20] Sheldrick G M. Program for Crystal Structure Solution [M]. Germany: University of Gttingen, 1990. [21] Sheldrick G M. Program for Crystal Structure Refinement [M]. Germany: University of Gttingen, 1997. [22] Parker C A, Rees W T. Correction of fluorescence spectra and measurement of fluorescence quantum efficiency [J]. Analyst, 1960, 85(1013):587-600. [23] Xu Q, Xiong W, Wang Q Q, et al. Synthesis, crystal structure, and characterization of 2,7-bis fluorine [J]. Chin. J. Struct. Chem.(结构化学), 2012, 31(10):1423-1428 (in Chinese). [24] Ma W B, Wu Y Q, Gu D H, et al. Study on the spectral properties of a new fluorene derivative [J]. Spectrosc. Spect. Anal.(光谱学与光谱分析), 2005, 25(8):1297-1300 (in Chinese). [25] Tirapattur S, Belletete M, Drolet N, et al. Steady-state and time-resolved studies of 2,7-carbazole-based conjugated polymers in solution and as thin films:determination of their solid state fluorescence quantum efficiencies [J]. Chem. Phys. Lett., 2003, 370(5):799-804. [26] Zhou E, Nakamura M, Nishizawa T, et al. Synthesis and photovoltaic properties of a novel low band gap polymer based on N-substituted dithieno pyrrole [J]. Macromolecules, 2008, 41(22):8302-8305. [27] Zeng G, Yu W L, Huang W, et al. Spectral and thermal spectral stability study for fluorene-based conjugated polymers [J]. Macromolecules, 2002, 35(18):6907-6914. [28] Hou Q, Zhou Q M, Zhang Y, et al. Synthesis and electroluminescent properties of high-efficiency saturated red emitter based on copolymers from fluorene and 4,7-di(4-hexylthien-2-yl)-2,1,3-benzothiadiazole [J]. Macromolecules, 2004, 37(17):6299-6305. [29] Teetsov J, Fox M A. Photophysical characterization of dilute solution and ordered thin films of alkyl-substituted polyfluorenes [J]. J. Mater. Chem., 1999, 9(9):2117-2122. [30] Liu Z P, Li X, Jiang J, et al. Synthesis, crystal structure and spectroscopic properties of 2,7-bis(3-cyanophenyl)-9,9-diethyl-fluorene [J]. Chin. J. Lumin.(发光学报), 2013, 34(5):579-584 (in English). [31] Li C J, You H J, Zhang Z Y, et al. Synthesis and optoelectronic properties of an arylamine-endcapped spirofluorene for blue light emission [J]. Chin. J. Org. Chem.(有机化学), 2011, 31(12):2095-2101 (in Chinese). [32] Gispert J R. Coordination Chemistry [M]. New York: Wiley, 2008:483-484. [33] Lai K Y, Chu T M, Elangovan A, et al. Excimer emission from a novel ethyne-based fluorescent dye in organic light-emitting devices [J]. Surf. Coat. Technol., 2006, 200(10):3283-3288. [34] Kotaka H, Konishi G, Mizuno K. Synthesis and photoluminescence properties of p-extended fluorene derivatives: The first example of a fluorescent solvatochromic nitro-group-containing dye with a high fluorescence quantum yield [J]. Tetrahedron Lett., 2010, 51:181-184.

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