电子受体芳基硼和电子给体吡咯[3,2-b]并吡咯杂化的新型有机发光分子的合成及其性质研究

李川, 刘欢, 叶俊, 张弛*

化工新型材料 ›› 2019, Vol. 47 ›› Issue (8) : 66 -69.

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化工新型材料 ›› 2019, Vol. 47 ›› Issue (8) : 66-69.
新材料与新技术

电子受体芳基硼和电子给体吡咯[3,2-b]并吡咯杂化的新型有机发光分子的合成及其性质研究

    李川, 刘欢, 叶俊, 张弛*
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Synthesis and property of a new organic luminescent molecule with electron acceptor aryl boron and electron donor pyrrole[3,2-b]pyrrole

  • Li Chuan, Liu Huan, Ye Jun, Zhang Chi
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摘要

富电子的吡咯[3,2-b]并吡咯具有特异的光电性能,硼是一种缺电子原子,利用其空的d轨道做电子受体单元,通过将2个单元相互结合,合成了一种新型含硼的吡咯[3,2-b]并吡咯发光分子(Mes2BPP),热降解温度为390.1℃,通过理论计算、光物理、电化学等表征手段研究了其结构和内在性能之间的关系,结果证明,该化合物在有机电致发光器件中具有巨大的潜力。

Abstract

Pyrrolo-[3,2-b]pyrroles possesses interesting optoelectronic properties.Boron atom is often used as an electron acceptor because of its empty d orbit.A new type pyrrolo-[3,2-b]pyrroles emitter containing boron atom unit was synthesized,and detailedly introduced its synthesis method and reaction mechanism.Its thermal degradation temperature was 390.1℃.Through thermogravimetric analysis and theoretical calculation,the photophysical,electrochemical properties were tested to research the relationship between its structure and properties.As a result,Mes2BPP had a great potentiality in the field of organic electroluminescence devices.

关键词

吡咯[3,2-b]并吡咯 / 芳基硼 / 有机发光分子

Key words

pyrrole-[3,2-b]pyrrole / aryl boron / organic fluorescent material

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电子受体芳基硼和电子给体吡咯[3,2-b]并吡咯杂化的新型有机发光分子的合成及其性质研究[J]. 化工新型材料, 2019, 47(8): 66-69 DOI:

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参考文献

[1] Krutosíkoví A,Gracza T.Recent studies in chemistry of hetero analogs of pentalene dianion[J].Scientfic Reports,2008,7711:1-7.
[2] Biswas A K,Das A,Ganguly B.Can fused-pyrrole rings act as better π-spacer units than fused-thiophene in dye-sensitized solar cells-a computational study[J].New Journal of Chemistry,2016,40(11):9304-9312.
[3] McCulloch I,Heeney M,Chabinyc M L,et al.Semiconducting thienothiophene copolymers:design,synthesis,morphology,and performance in thin-film organic tran-sistors[J].Adv Mater,2009,21:1091-109.
[4] Roncali J.Conjugated poly (thiophenes):synthesis,functionalization,and applications[J].Chemical Reviews,1992,92(4):711-738.
[5] Jin Y E,Kim K,Song S,et al.New conjugated polymer based on dihydroindoloindole for LEDs[J].Bulletin of the Korean Chemical Society,2006,27(7):1043-1047.
[6] Capan A,Veisi H,Goren A C,et al.Concise syntheses,polymers,and properties of 3-arylthieno [3,2-b] thiophenes[J].Macromolecules,2012,45(20):8228-8236.
[7] Fuller L S,Iddon B,Smith K A.Thienothiophenes synthesis,metallation and bromine→lithium exchange reactions of thieno [3,2-b] thiophene and its polybromo derivatives[J].Journal of the Chemical Society(Perkin Transactions 1),1997(22):3465-3470.
[8] Henssler J T,Zhang X,Matzger A J.Thiophene/thieno [3,2-b] thiophene co-oligomers:fused-ring analogues of sexithiophene[J].The Journal of Organic Chemistry,2009,74(23):9112-9119.
[9] Kim J,Han A R,Seo J H,et al.β-Alkyl substituted dithieno [2,3-d;2′,3′-d′] benzo [1,2-b;4,5-b′] dithiophene semiconducting materials and their application to solution-processed organic transistors[J].Chemistry of Materials,2012,24(17):3464-3472.
[10] Koh K,Wong-Foy A G,Matzger A J.A porous coordination copolymer with over 5000m2/g BET surface area[J].Journal of the American Chemical Society,2009,131(12):4184-4185.
[11] Kuhn M,Falk F C,Paradies J.Palladium-catalyzed C—S coupling:access to thioethers,benzo [b] thiophenes,and thieno [3,2-b] thiophenes[J].Organic Letters,2011,13(15):4100-4103.
[12] Nenajdenko V G,Sumerin V V,Chernichenko K Y,et al.A new route to annulated oligothiophenes[J].Organic Letters,2004,6(20):3437-3439.
[13] Orłowski R,Banasiewicz M,Clermont G,et al.Strong solvent dependence of linear and non-linear optical properties of donor-acceptor type pyrrolo [3,2-b] pyrroles[J].Physical Chemistry Chemical Physics,2015,17(37):23724-23731.
[14] Friese D H,Mikhaylov A,Krzeszewski M,et al.Pyrrolo [3,2-b] pyrroles—from unprecedented solvatofluorochromism to two-photon absorption[J].Chemistry-A European Journal,2015,21(50):18364-18374.
[15] Krzeszewski M,Kodama T,Espinoza E M,et al.Nonplanar butterfly-shaped π-expanded pyrrolopyrroles[J].Chemistry-A European Journal,2016,22(46):16478-16488.
[16] Tanaka S,Kumagai T,Mukai T,et al.1,4-Dihydropyrrolo [3,2-b] pyrrole:the electronic structure elucidated by photoelectron spectroscopy[J].Bulletin of the Chemical Society of Japan,1987,60(6):1981-1983.
[17] Hayase F,Takahashi Y,Tominaga S,et al.Identification of blue pigment formed in a d-xylose-glycine reaction system[J].Bioscience,Biotechnology,and Biochemistry,1999,63(8):1512-1514.
[18] Sasaki S,Shirahashi Y,Nishiyama K,et al.Identification of a novel blue pigment as a melanoidin intermediate in the d-xylose-glycine reaction system[J].Bioscience,Biotechnology,and Biochemistry,2006,70(10):2529-2531.
[19] Shirahashi Y,Watanabe H,Hayase F.Identification of red pigments formed in a d-xylose-glycine reaction system[J].Bioscience,Biotechnology,and Biochemistry,2009,73(10):2287-2292.
[20] Wu J Y,Yu C H,Wen J J,et al.Pyrrolo-[3,2-b] pyrroles for photochromic analysis of halocarbons[J].Analytical Chemistry,2015,88(2):1195-1201.
[21] Canjeevaram Balasubramanyam R K,Kumar R,Ippolito S J,et al.Quadrupolar (A-π-D-π-A) tetra-aryl 1,4-dihydropyrrolo [3,2-b] pyrroles as single molecular resistive memory devices:substituent triggered amphoteric redox performance and electrical bistability[J].The Journal of Physical Chemistry C,2016,120(21):11313-11323.
[22] Lee M W,Kim J Y,Son H J,et al.Tailoring of energy levels in D-π-A organic dyes via fluorination of acceptor units for efficient dye-sensitized solar cells[J].Scientific Reports,2015,5:1-6.
[23] Fuse S,Sugiyama S,Maitani M M,et al.Elucidating the structure-property relationships of donor-π-acceptor dyes for dye-sensitized solar cells (DSSCs) through rapid library synthesis by a one-pot procedure[J].Chemistry-A European Journal,2014,20(34):10685-10694.
[24] Liu X,Kong F,Guo F,et al.Influence of π-linker on triphenylamine-based hole transporting materials in perovskite solar cells[J].Dyes and Pigments,2017,139:129-135.
[25] Holzer B,Bintinger J,Lumpi D,et al.Color fine-tuning of optical materials through rational design[J].Chem Phys Chem,2017,18(5):549-563.
[26] Soldano C,D'Alpaos R,Generali G.Highly efficient red organic light-emitting transistors (OLETs) on high-k dielectric[J].ACS Photonics,2017,4(4):800-805.
[27] Che X,Chung C L,Liu X,et al.Regioisomeric effects of donor-acceptor-acceptor′ small-molecule donors on the open circuit voltage of organic photovoltaics[J].Advanced Materials,2016,28(37):8248-8255.
[28] Noh Y Y,Kim D Y,Yoshida Y,et al.High-photosensitivity p-channel organic phototransistors based on a biphenyl end-capped fused bithiophene oligomer[J].Applied Physics Letters,2005,86(4):043501-043509.
[29] Ye J,Chen Z,Fung M K,et al.Carbazole/sulfone hybrid D-π-A-structured bipolar fluorophores for high-efficiency blue-violet electroluminescence[J].Chem Mater,2013,25(13):2630-2637.

基金资助

国家自然科学基金(51603088,21267003);江苏省自然科学基金(BK20150154)

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