The Spectroscopic Behavior of Dicyanovinyldithienothiophenes

doi:10.7517/j.issn.1674-0475.2009.01.16

Abstract

Abstract: Two conjugated D-A compounds,2-dicyanovinlydithieno[3,2-b:2’,3’-d]thiophene(DCTT) and 2-dicyanovinlydithieno[2,3-b:3’,2’-d]thiophene(DCST) were synthesized and characterized.The relationship between the emission properties and molecular structures was studied by investigation of solvent effect for DCTT and DCST.Both title compounds show intramolecular charge transfer(ICT) state emission.With the increase of polarity of solvents,DCST shows ICT emission with strong red shift and larger Stokes shift.However,DCTT shows weak red shift but negative solvatochromism: an increase of quantum yields from ICT emission,which may due to the Proximity effect between the transitions of π-π^* and n-π^*.Such emission difference between DCTT and DCST shows that the ICT state could be occurred in both compounds,but charge separation might not be formed easily between moiety of thieno[3,2-b:2’,3’-d]thiophene and moiety of dicyanovinyl in DCTT,however,formed easily between moiety of thieno[2,3-b:3’,2’-d]thiophene and moiety of dicyanovinyl in DCST.

Key words: 2-dicyanovinlydithieno[3,2-b’,3’-d]thiophene, 2-dicyanovinlydithieno[2,3-b’,2’-d]thiophene, synthesis, ICT state emission, solvent effect

CLC Number:

ZHAO Chun-mei, XU Li, SHI Jian-wu, WANG Hua. The Spectroscopic Behavior of Dicyanovinyldithienothiophenes[J]. Imaging Science and Photochemistry, 2009, 27(1): 16-22.

References

[1] Batista R M F,Costa S P G,Raposo M M M.Synthesis of new fluorescent 2-(2′,2′-bithienyl)-1,3-benzothiazoles[J].Tetrahedron Letters,2004,45:2825-2828.
[2] 王志强,朱艳艳,黄达,万婧,彭兆快,张晓宏.蓝光材料2-叔丁基-9,10-二(9,9-二正丙基芴基)蒽的合成与性能征[J].感光科学与光化学(影像科学与光化学),2007,25(6):415-421.Wang Z Q,Zhu Y Y,Huang D,Wan J,Peng Z K,Zhang X H.Synthesis and characterization of the soluble blue light emitting material 2-tert-butyl-9,10-bis(9,9-dipropylfluorenyl) anthracene[J].Photographic Science and photochemistry(Imaging Science and Photochemistry),2007,25(6):415-421.
[3] Mashraqui S H,Ghadigaonkar S,Das P K.Optically transparent and thermally stable nonlinear optic chromophores featuring a thieno[2,3-b] thiophene donor[J].Tetrahedron,2007,63:10011-10017.
[4] Itami K,Yamazaki D,Yoshida J I.Pyrimidine-core extended π-systems:general synthesis and interesting fluorescent properties[J].J.Am.Chem.Soc.,2004,126:15396-15397.
[5] Sun Y M,Ma Y Q,Liu Y Q,et al.High-performance and stable organic thin-film transistors based on fused thiophenes[J].Adv.Funct.Mater.,2006,16:426-432.
[6] Xiao K,Liu Y Q,et al.A Highly π-stacked organic semiconductor for field effect transistors based on linearly condensed pentathienoacene[J].J.Am.Chem.Soc.,2005,127:13281-13286.
[7] Zhao D F,Xu L,Wang H.Formylation and diformylation of dithieno[2,3-b:3′,2′-d] thiophene and dithieno-[3,2-b:2′,3′-d] thiophene[J].J.Henan Univ.(Natural Science),2007,37(5):468-473.
[8] Bilot L,Kawaski A.Theory of the effect of solvents on the electron spectra of molecules[J].Z.Naturforsch.,1962,17A:621-627.
[9] 李洁,王华,郝玉英,等.1,5-萘二胺衍生物的合成及发光行为[J].发光学报,2005,26(2):247-252.Li J,Wang H,Hao Y Y,et al.Synthesis and photoluminescent properties of 1,5-naphthalene diamine derivative[J].Chinese Journal of Luminescene,2005,26(2):247-252.
[10] 张联齐,张宝文,曹怡.5位芘取代的三芳基吡唑啉化合物的光物理行为[J].物理化学学报,1999,15(10):911-917.Zhang L Q,Zhang B W,Cao Y.A study on photophysical behavior of 1,3-diphenyl-5-(2)-pyrenyl-2-pyrazoline[J].Acta Physico-Chimica Sinica,1999,15(10):911-917.
[11] 吴世康.具有荧光发射能力有机化合物的光物理和光化学问题研究[J].化学进展,2005,17(1):15-39.Wu S K.The problem on photophysics and photochemistry of organic compounds possessing ability of fluorescence emission[J].Progress in Chemistry,2005,17(1):15-39.
[12] Lai T I,Lim B T,Lim E C.Photophysical properties of biologically important molecules related to proximity effects:psoralens[J].J.Am.Chem.Soc.,1982,104:7631-7635.
[13] 王华,张宝文,曹怡.对硝基苯乙基蒽的光谱行为的研究[J].科学通报,1996,41(13):1185-1190.Wang H,Zhang B W,Cao Y.Study on the spectroscopic behavior of 2-(4-nitro-phenyl)vinyl anthracene[J].Chinese Science Bulletin,1996,41(13):1185-1190.

[1]	ZHU Tao, ZHANG Yan, DONG Lulu, GUO Pengyue, YANG Dongzhi. Biomimetic Synthesis of Au QDs and the Application of Glucose Detection in Serum [J]. Imaging Science and Photochemistry, 2020, 38(6): 941-949.
[2]	TAO Pingfang, FENG Yuqin, ZHOU Neng, QIN Liqin, ZHANG Pei. Hydrothermal Synthesis of α-NaYF₄: Ce³⁺/Tb³⁺ Nanospheres with High Fluorescence Properties [J]. Imaging Science and Photochemistry, 2018, 36(2): 161-170.
[3]	JI Haixia, DONG Lulu, DU Yan, YAO Xinyue, YANG Dongzhi. Biomimetic Synthesis of CdS Quantum Dots in Living Cancer Cells [J]. Imaging Science and Photochemistry, 2018, 36(1): 57-63.
[4]	ZENG Ze, ZHONG Rong, ZHANG Chunhui, XIE Gang. Synthesis and Properties of Phenylglyoxylic Acid Ester/2959 Photoinitiator [J]. Imaging Science and Photochemistry, 2017, 35(6): 808-815.
[5]	DENG Yafeng, ZHOU Yihua, QIAN Jun, LUO Yan, WU Lihui. Preparation and Application of Carbon Quantum Dots Based on Up Conversion Photoluminescence [J]. Imaging Science and Photochemistry, 2017, 35(6): 884-893.
[6]	WANG Hua. Chemical and Photochemical Synthesis of Thiophene-based Helicenes [J]. Imaging Science and Photochemistry, 2017, 35(5): 603-613.
[7]	ZHANG Qingbao, LIU Qiang. Applications of Visible-light-driven Aerobic Oxidation in Organic Synthesis [J]. Imaging Science and Photochemistry, 2017, 35(5): 614-625.
[8]	CAO Yitao, WU Lizhu, TONG Zhenhe(TUNG Chenho), ZHANG Tierui. Photochemical Synthesis of Inorganic Nanomaterials [J]. Imaging Science and Photochemistry, 2017, 35(5): 642-648.
[9]	GUI Mengxi, YU Yang, ZHU Chengyi, LIU Hongfang, WANG Feng. Advances on Molecular Systems for Photocatalytic CO₂ Reduction Based on Cobalt Complexes as Catalysts [J]. Imaging Science and Photochemistry, 2017, 35(5): 649-657.
[10]	LEI Yuan, ZHANG Sai, GAO Jun. Synthesis,Structure and Photochromic Properties of N-ethyl-9'-n Bromobutoxy Spirooxazine and Its Modified PMMA [J]. Imaging Science and Photochemistry, 2016, 34(6): 526-533.
[11]	JIANG Wei, WU Xiang. Hydrothermal Synthesis and Photocatalytic Properties of ZnS Microflowers [J]. Imaging Science and Photochemistry, 2016, 34(3): 252-256.
[12]	YANG Ke, ZHANG Yan, XU Jianhua. The Application of Electron Transfer Photo-oxidation Reaction in Organic Synthesis [J]. Imaging Science and Photochemistry, 2014, 32(5): 433-446.
[13]	LI Bing, XIA Wujiong. Solid-state Asymmetric Photochemistry of Bicyclo[3.1.0] hexyl Ketone Carbonyl Derivatives [J]. Imaging Science and Photochemistry, 2014, 32(5): 455-462.
[14]	LIANG Qinghua, SHI Yao, MA Wangjing, YANG Xinmin, LI Zhi. Hydrothermal Synthesis and Characterization of Ba₇F₁₂Cl₂：Eu²⁺ Used for X-ray Imaging Plate [J]. Imaging Science and Photochemistry, 2014, 32(2): 150-156.
[15]	LI Bo, HUANG Zhongbing, MENG Xianwei, TANG Fangqiong. Hydrothermal Synthesis and Application of the Fe₃O₄ Nanoparticles Modified with L-cysteine [J]. Imaging Science and Photochemistry, 2014, 32(2): 163-170.