Study on AIE Emission of (E)-N-4-(2-(5-dicyanovinly-dithieno-[2,3-b:3',2'-d]thiophene-2-yl)ethenyl)-N,N-diphenylamine

doi:10.7517/j.issn.1674-0475.2016.05.465

Abstract

Abstract:

A dithieno[2,3-b:3',2'-d]thiophene bridged D-A compound, (E)-N-4-(2-(5-dicyanovinly-dithieno[2,3-b:3',2'-d]thiophene-2-yl)-ethenyl)-N,N-diphenylamine (TPA-DCST) was synthesized and its spectroscopic behaviors were studied. In the section of synthesis, TPA-DCST was synthesized by Wittig reaction between two moieties of triphenyl amine and dithieno[2,3-b:3',2'-d]thiophene-2-carbaldehyde, and the following formylation of dithieno[2,3-b:3',2'-d]thiophene moiety and Knoevenagel condensation with malononitrile. The target compound TPA-DCST was fully characterized by ¹HNMR, ¹³CNMR, IR and HRMS. In the section of the spectroscopic behaviors, both absorption and emission behaviors of TPA-DCST were studied. The absorption peak at ~412 nm belongs to π-π^* transition. TPA-DCST shows an interesting broad emission at 550 nm in diluted hexane solution, which is regarded as an emission from molecular aggregation, and confirmed by its single peak emission at 460 nm in CTAB micelle solution ([c]=1.02×10^-2 mol/L). No ICT emission was observed in different polar solvents, because the conjugation bridge, dithieno[2,3-b:3',2'-d]thiophene does not show the effective function of conjugation due to the molecular structure itself. Both concentration effect and temperature effect show that TPA-DCST molecules are easy to give the emission from molecular aggregation. In THF-H₂O binary mixture solution, TPA-DCST shows typical AIE state emission at 692 nm. With increasing aggregation of TPA-DCST molecules, the emission peak shows strong bathochromic shift, from 550 nm in hexane solution to 710 nm in solid. The driving force of the aggregation may be from hydrophobic effect and dipole-dipole interaction of TPA-DCST molecules.

Key words: D-A compound, dithieno[2,3-b:3',2'-d]thiophene conjugated bridge, concentration effect, temperature effect, aggregation-induced emission

GAO Xiuxiu, ZHANG Yongqing, LI Chunli, WANG Hua. Study on AIE Emission of (E)-N-4-(2-(5-dicyanovinly-dithieno-[2,3-b:3',2'-d]thiophene-2-yl)ethenyl)-N,N-diphenylamine[J]. Imaging Science and Photochemistry, 2016, 34(5): 465-474.

References

[1] Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Kwok H S, Zhan X W, Liu Y Q, Zhu D B, Tang B Z. Aggregatin-induced emission of 1-methyl-1,2,4,5-pentaphenylsilole[J]. Chemical Communications, 2001, 18: 1740-1741.
[2] Zhao Z J, Lam J W Y, Tang B Z. Aggregation-induced emission of luminogens[J].Current Organic Chemistry, 2010, 14: 2109-2132.
[3] 曾毅,李鹏,李嫕. 四苯基乙烯衍生物光物理和光化学研究[J]. 影像科学与光化学, 2014, 32: 463-470. Zeng Y, Li P, Li Y. Photophysical and photochemical studies on a tetraphenylethene derivative[J]. Imaging Science and Photochemistry, 2014, 32: 463-470.
[4] Hirano K, Minakata S, Komatsu M, Mizuguchi J. Intense blue luminescence of 3,4,6-triphenyl-alpha-pyrone in the solid state and its electronic characterization[J]. The Journal of Physcical Chemistr A, 2002, 106: 4868-4871.
[5] Li Z, Dong Y Q, Mi B X, Tang Y H, Haussler M, Tong H, Dong Y P, Lam J W Y, Ren Y, Sung H H Y, Wong K S, Gao P, Williams I D, Kwok H S, Tang B Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials[J]. The Journal of Physcical Chemistry B, 2005, 109: 10061-10066.
[6] Mei J, Hong Y, Lam J W Y, Qin A, Tang Y, Tang B Z. Aggregation-induced emission: the whole is more brilliant than the parts[J]. Advanced Materials, 2014, 26: 5429-5479.
[7] Ma K, Li X, Xu B, Tian W. A sensitive and selective "turn-on" fluorescent probe for Hg²⁺ based on thymine-Hg²⁺-thymine complex with an aggregation-induced emission feature[J]. Analysis Methods, 2014, 6: 2338-2342.
[8] Liang G D, Lam J W Y, Qin W, Li J, Xie N, Tang B Z. Molecular luminogens based on restriction of intramolecular motions through host-guest inclusion for cell imaging[J]. Chemical Communications, 2014, 50: 1725-1727.
[9] Scalise R E, Caradonna P A, Tracy H J, Mullin J L, Keirstead A E. 1,1-Dimethyl-2,3,4,5-tetraphenylsilole as a molecular rotor probe to investigate the microviscosity of imidazolium ionic liquids[J]. Journal of Inorganic Organometallic Polymers and Materials, 2014, 24: 431-441.
[10] Shi J W, Li Y B, Jia M, Xu L, Wang H. Organic semiconductors based on annelated boligothiophenes and its application for organic field-effect transistors[J]. Journal of Materials Chemistry, 2011, 8: 17612-17614.
[11] Shi J W, Xu L, Li Y B, Jia M, Kan Y H, Wang H. Intermolecular interactions in organic semiconductors based on annelated β-oligothiophenes and their effect on the performance of organic field-effect transistors[J]. Organic Electronics, 2013, 14: 934-941.
[12] Yang H Y, Yen Y S, Hsu Y C, Chou H H, Lin J T. Organic dyes incorporating the dithienothiophene moiety for efficient dye-sensitized solar cells[J]. Organic Letters, 2010, 12: 16-19.
[13] 赵春梅, 徐莉, 史建武, 王华. 二氰基乙烯基并三噻吩的光谱行为[J]. 影像科学与光化学, 2009, 27: 16-22.Zhao C M, Xu L, Shi J W, Wang H. The spectroscopic behavior of dicyanovinyldithienothiophenes[J]. Imaging Science and Photochemistry, 2009, 27: 16-22.
[14] Suffert J. Simple direct titration of organolithium reagents using N-pivaloyl-o-toluidine and/or N-pivaloyl-o-benzylaniline[J]. Journal of Organic Chemistry, 1989, 54: 509-510.
[15] Li C L, Zhang Y Q, Zhang S, Shi J W, Kan Y H, Wang H. From N,N-diphenyl-N-naphthothieno[2,3-b:3',2'-d]dithiophene-5-yl-amine to propeller-shaped N,N,N-tri(naphthothieno[2,3-b:3',2'-d]dithiophene-5-yl)-amine: syntheses and structures[J]. Tetrahedron, 2014, 70: 3909-3914.
[16] 刘派, 陈笛笛, 冯霄, 石建兵, 佟斌, 董宇平. 多芳基吡咯衍生物的发光性质及其应用[J]. 影像科学与光化学, 2015, 33: 441-460. Liu P, Chen D D, Feng X, Shi J B, Tong B, Dong Y P. Emission properties and application of multiaryl-substituted pyrroles[J]. Imaging Science and Photochemistry, 2015, 33: 441-460.
[17] Qian L J, Tong B, Shen J B, Shi J B, Zhi J G, Dong Y Q, Yang F, Dong Y P, Lam J W Y, Liu Y, Tang B Z. Crystallization-induced emission enhancement in a phosphorus-containing heterocyclic luminogen[J]. Journal of Physical Chemistry B, 2009, 113: 9098-9103.
[18] 唐海云, 曾毅, 李迎迎, 陈金平, 李嫕. α-吡喃酮衍生物的合成及聚集荧光增强性质研究[J]. 化学学报, 2011, 69: 2241-2247. Tang H Y, Zeng Y, Li Y Y, Chen J P, Li Y. Synthesis and aggregation-induced emission of a novel α-pyrone derivative[J]. Acta Chimica Sinica, 2011, 69: 2241-2247.