Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives

Chun-yu CUI; Xiao-yang QIU; Qi QI; Xing LI

doi:10.37188/fgxb20204107.0809

您当前的位置：

首页 >

文章列表页 >

Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives

Synthesis and Properties of Materials | 更新时间：2020-09-10

- Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives
- Chinese Journal of Luminescence Vol. 41, Issue 7, Pages: 809-818(2020)
- 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.宁波大学科学技术学院, 浙江慈溪 315212
  3.中国科学院福建物质结构研究所结构化学国家重点实验室, 福建福州 350002
- 作者简介：
- 基金信息：
  
  Supported by National Natural Science Foundation of China;Natural Science Foundation
- DOI：10.37188/fgxb20204107.0809
  CLC：
扫描看全文
Chun-yu CUI, Xiao-yang QIU, Qi QI, et al. Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives. [J]. Chinese Journal of Luminescence 41(7):809-818(2020)
DOI：

Chun-yu CUI, Xiao-yang QIU, Qi QI, et al. Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives. [J]. Chinese Journal of Luminescence 41(7):809-818(2020) DOI： 10.37188/fgxb20204107.0809.

摘要

通过Suzuki偶联反应，用不同基团对双噻吩原料上的溴原子进行取代后合成了一系列双噻吩衍生物：3-（5'-溴-[2，2-双噻吩]-5-基）吡啶（Dt-1）、5，5-双（吡啶-3-基）-2，2-双噻吩（Dt-2）、5-（3，5-双（三氟甲基）苯基）-2，2-双噻吩（Dt-3）、5，5-双（3，4，5-三氟苯基）-2，2-双噻吩（Dt-4）。通过红外光谱（IR）、质谱（MS）、核磁共振氢谱（,1,H NMR）及单晶X射线衍射对其结构进行了表征。通过紫外-可见吸收光谱和荧光光谱研究了其发光性能。结果表明，在CH,2,Cl,2,溶液中，化合物Dt-1在349 nm激发光作用下在390~470 nm区域有较强的双荧光发射行为，两个最大发射峰分别为403 nm和422 nm；化合物Dt-2在372 nm激发光作用下在400~480 nm区域即紫色和蓝色光区有较强的双荧光发射行为，最大发射峰分别为430 nm和440 nm；化合物Dt-3在349 nm激发光作用下在418 nm处有最强的荧光发射；化合物Dt-4在371 nm激发光作用下于436 nm处有最强的荧光发射。由于双噻吩共轭结构中引入的吸/给电子基团增加了π电子的流动性以及共轭程度，增强了分子间的相互作用力，振动弛豫现象以及斯托克斯位移（Stokes shifts）的产生引发的能量损失导致最大吸收峰向长波方向移动。

Abstract

A series of bisthiophene derivatives were synthesized by Suzuki coupling reaction, in which bromine atoms on bisthiophene raw materials were substituted with different groups: 3-(5'-bromo-[2, 2-bisthiophene]-5-yl)pyridine(C,13,H,8,BrNS,2,M,r,=322.24, compound Dt-1), 5, 5-bis(pyridine-3)-yl)-2, 2-bisthiophene(C,18,H,12,N,2,S,2,M,r,=320.43, compound Dt-2), 5-(3, 5-bis (trifluoromethyl)phenyl) -2, 2-bisthiophene(C,16,H,8,F,6,S,2,M,r,=378.35, compound Dt-3), 5, 5-bis(3, 4, 5-trifluoro-phenyl)-2, 2-bithiophene(C ,20,H,8,F,6,S,2,M,r,=426.39, compound Dt-4). The structures were characterized by infrared spectroscopy(IR), mass spectrometry(MS), nuclear magnetic resonance spectroscopy(,1,H NMR) and single crystal X-ray diffraction. The luminescence properties were studied by UV-Vis absorption spectroscopy and fluorescence spectroscopy. The results showed that compound Dt-1 had strong fluorescence emission ranging from 390 nm to 470 nm under the excitation light of 349 nm in CH,2,Cl,2, solution, and the two largest emission peaks are 403 nm and 422 nm, respectively. Compound Dt-2 showed strong fluorescence emission in the 400－480 nm region under the excitation light of 372 nm with two maximum emission peaks at 430 nm and 440 nm. Compound Dt-3 exhibited the strongest fluorescence emission at 418 nm under excitation light of 350 nm and compound Dt-4 presented the strongest fluorescence emission at 436 nm under 371 nm excitation light. Due to the introduction of electron-withdrawing/donating groups in the conjugated structure of bisthiophene, the mobility and conjugation degree of π electrons are increased, and the intermolecular interaction force is enhanced. Energy loss caused by vibration relaxation phenomenon and Stokes shift leads to the shifts of the maximum absorption peaks to the long wave direction.

关键词

双噻吩衍生物合成晶体结构光谱性能

Keywords

bisthiophene derivativesynthesiscrystal structuresspectral properties

references

TAO P, MIAO Y Q, WANG H, et al.. High-performance organic electroluminescence:design from organic light-emitting materials to devices[J].Chem. Rec., 2019, 19(8):1531-1561.

刘俞汝.几种空穴传输材料的合成及电化学性能研究[D].郑州: 郑州大学, 2017.

LIU Y R. Synthesis and Photoelectrochemical Performance Study of Several Hole-transport materials [D]. Zhengzhou: Zhengzhou University, 2017. (in Chinese)

ASHOK KUMAR S, SHANKAR J S, PERIYASAMY B K, et al.. Device engineering aspects of organic light-emitting diodes (OLEDs)[J].Polym. Plast. Technol. Mater., 2019, 58(15):1597-1624.

JEON Y, CHOI H R, KWON J H, et al.. Sandwich-structure transferable free-form OLEDs for wearable and disposable skin wound photomedicine[J].Light Sci. Appl., 2019, 8:114-1-15.

LU R M, HAN Y, ZHANG W M, et al.. Alkylated indacenodithieno[3, 2-b] thiophene-based all donor ladder-type conjugated polymers for organic thin film transistors[J].J. Mater. Chem. C, 2018, 6(8):2004-2009.

MCAFEE S M, DAYNEKO S V, JOSSE P, et al.. Simply complex:the efficient synthesis of an intricate molecular acceptor for high-performance air-processed and air-tested fullerene-free organic solar cells[J].Chem. Mater., 2017, 29(3):1309-1314.

KHOUND S, SARMA R. Low-voltage organic thin film transistors (OTFTs) using crosslinked polyvinyl alcohol (PVA)/neodymium oxide (Nd2O3) bilayer gate dielectrics[J].Appl. Phys. A, 2018, 124(1):41-1-6.

LI X, LI Z, YANG Y W. Tetraphenylethylene-interweaving conjugated macrocycle polymer materials as two-photon fluorescence sensors for metal ions and organic molecules[J].Adv. Mater., 2018, 30(20):1800177-1-7.

SHI Z Q, LI Y Z, GUO Z J, et al.. Six new 2D or 3D metal-organic frameworks based on bithiophene-containing ligand and dicarboxylates:syntheses, structures, and properties[J].Cryst. Growth Des., 2013, 13(7):3078-3086.

LI L Q, WANG L Y, TANG H, et al.. A facile synthesis of novel near-infrared pyrrolopyrrole aza-BODIPY luminogens with aggregation-enhanced emission characteristics[J].Chem. Commun., 2017, 53(59):8352-8355.

MORIGUCHI T, YAKEYA D, TSUGE A, et al.. Synthesis of three new thiophene condensed pyrene derivatives, crystal structure and evaluation of their photophysical properties[J].J. Mol. Struct., 2018, 1157:348-354.

RIZWAN K, ZUBAIR M, RASOOL N, et al.. Palladium(0) catalyzed Suzuki cross-coupling reaction of 2, 5-dibromo-3-methylthiophene:selectivity, characterization, DFT studies and their biological evaluations[J].Chem. Cent. J., 2018, 12:49-1-12.

刘威, 陈厚和.一维含能金属有机框架的合成与性能研究[J].材料导报, 2018, 32(2):223-227.

LIU W, CHEN H H. 1D energetic metal-organic frameworks:synthesis and properties[J].Mater. Rev., 2018, 32(2):223-227. (in Chinese)

KHALI M, ULLAH M A, ADEEL M, et al.. Synthesis, crystal structure analysis, spectral IR, UV-Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives:interplay of experimental and DFT study[J].J. Saudi Chem. Soc., 2019, 23(5):546-560.

SHELDRICK G M. Program for Crystal Structure Solution and Refinement [M]. Gottingen:University of Göttingen, 1997.

SHELDRICK G M. Program for Crystal Structure Refinement [M]. Germany:University of Göttingen, 1997.

PARKER C A, REES W T. Correction of fluorescence spectra and measurement of fluorescence quantum efficiency[J].Analyst, 1960, 85(1013):587-600.

CHEN R F. Fluorescence quantum yields of tryptophan and tyrosine[J].Anal. Lett., 1967, 1(1):35-42.

RANGASAMY M, PALANINATHAN K. Thiophene and furan appended pyrazoline based fluorescent chemosensors for detection of Al3+ ion[J].Inorg. Chem. Commun., 2019, 101:177-183.

LIN Y D, ABATE S Y, CHUNG H C, et al.. Donor-acceptor-donor type cyclopenta[2, 1-b; 3, 4-b'] dithiophene derivatives as a new class of hole transporting materials for highly efficient and stable perovskite solar cells[J].ACS Appl. Energy Mater., 2019, 2(10):7070-7082.

王碧, 席宏波, 周岳溪, 等.不同取代基对苯系物三维荧光光谱特征的影响[J].光谱学与光谱分析, 2017, 37(12):3763-3770.

WANG B, XI H B, ZHOU Y X, et al.. Effects of different substituents on three dimensional fluorescence properties of BTEX[J].Spectrosc. Spect. Anal., 2017, 37(12):3763-3770. (in Chinese)

BEDIER R A, YOUSEF T A, EL-REASH G M A, et al.. Synthesis, structural, optical band gap and biological studies on iron(Ⅲ), nickel (Ⅱ), zinc (Ⅱ) and mercury (Ⅱ) complexes of benzyl α-monoxime pyridyl thiosemicarbazone[J].J. Mol. Struct., 2017, 1139:436-446.

ZHOU E J, NAKAMURA M, NISHIZAWA T, et al.. Synthesis and photovoltaic properties of a novel low band gap polymer based on N-substituted dithieno[3, 2-b:2', 3' -d] pyrrole[J].Macromolecules, 2008, 41(22):8302-8305.

ZENG G, YU W L, CHUA S J, et al.. Spectral and thermal spectral stability study for fluorene-based conjugated polymers[J].Macromolecules, 2002, 35(18):6907-6914.

张松.两种新型芴衍生物的合成与性能研究[J].太原理工大学学报, 2014, 45(5):581-586.

ZHANG S. Synthesis and properties of two novel fluorene-based derivatives[J].J. Taiyuan Univ. Technol., 2014, 45(5):581-586. (in Chinese)

钱永, 王建军, 张蓉, 等. 1, 1-二(苯并咪唑-2-基)-2-(N-乙基咔唑-3-基)乙烯的合成及其性能研究[J].发光学报, 2014, 35(6):660-665.

QIAN Y, WANG J J, ZHANG R, et al.. Synthesis and properties of 1, 1-bis (benzo imidazole-2-yl)-2-(N-ethyl carbazole-3-yl) ethylene[J].Chin. J. Lumin., 2014, 35(6):660-665. (in Chinese)

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 Y Y, LIU Z P, ZHAO X H, et al.. Synthesis, crystal structure and spectroscopic properties of two fluorene-based derivatives[J].Chin. J. Lumin., 2014, 35(2):156-164. (in Chinese)

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Growth and Luminescence Properties of Tb³⁺ Ions Doped CaF₂ Crystals

Crystal Growth, Spectral Properties and Energy Transfer Mechanisms of Sr₃Gd（BO₃）₃∶Dy³⁺/RE³⁺（RE=Tb, Eu） Crystals

Synthesis and Optical Properties of Barium Doped CsPbBr₃ Blue Luminescence Quantum Dots

Photoluminescent Composite Materials by Embedding Carbon Dots in Zeolites

Synthesis, Luminescence Mechanism and Applications of Carbon Dots with Afterglow

Related Author

No data

Related Institution

State Key Laboratory of High-performance Ceramics and Superfine Microstructure， Shanghai Institute of Ceramics， Chinese Academy of Sciences

Jiangsu Key Laboratory of Advanced Laser Materials and Devices， School of Physics and Electronic Engineering， Jiangsu Normal University

School of Physics Science and Engineering， Institute for Advanced Study， Tongji University

Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China （Mindu Innovation Laboratory）

College of Chemistry， Fuzhou University

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰