PDF (1315K)
摘要
以富电子基团吡咯并[3,2-b]吡咯作为电子给体,在其2,5取代位上修饰不同的电子受体,设计合成了两个D-π-A结构的有机荧光材料2,5-二(4-(苯磺酰基)苯基)-1,4-二(4-叔丁基苯基)吡咯并[3,2-b]吡咯(DPSPP)和2,5-二(5,5-二氧-2-二苯并噻吩基)-1,4-二(4-叔丁基苯基)吡咯并[3,2-b]吡咯(BTPP)。通过热重分析研究了其热稳定性,通过紫外-可见吸收光谱、荧光光谱以及电化学法系统分析了其光致发光性能和结构的关系。通过改变吸电子能力以及共轭程度的大小,实现了发光光谱从蓝光到绿光的系统调节并伴随较高的荧光量子产率达到90%以上,在有机发光领域具有潜在的应用前景。
Abstract
Two new D-π-A organic fluorescent materials DPSPP (2,5-Bis(4-(phenylsulfonyl)phenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole) and BTPP (2,5-Bis(5,5-dioxo-2-dibenzothiophene)-1,4-bis (4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole) which modified the less well-known electron-rich pyrrole[3,2-b]pyrrole (PP) unit with different electron acceptors were systematically designed and then synthesized.The relationship of their photoluminescence properties and structure was investigated via TG,optical measurement and cyclic voltammetry.Using electron acceptor of stronger electron-withdrawing ability (or with larger π conjugation) was demonstrated an effective way to extend the fluorescence from blue (DPSPP) to green (BTPP),coupled with high fluorescence quantum efficiency (larger than 90%).All these showed the great potential for optoelectronic fields as organic fluorescent materials.
关键词
二吡咯
/
有机荧光材料
/
合成
/
性质
Key words
pyrrole-[3,2-b]pyrrole
/
organic fluorescent material
/
synthesis
/
property
新型二吡咯类有机荧光材料的合成及其性能研究[J].
化工新型材料, 2018, 46(8): 244-246 DOI:
[1] Lu H G,Zheng Y D,Zhao X W,et al.Highly efficient far red/near-infrared solid fluorophores:aggregation-induced emission,intramolecular charge transfer,twisted molecular conformation,and bioimaging applications[J].Angew Chem Int Ed,2016,55(1):155-159.
[2] Dong M S,Whitten D G.Solvatochromic behavior of intramolecular charge-transfer diphenylpolyenes in homogeneous solution and microheterogeneous media[J].J Phys Chem,1988,92(10):2945-2956.
[3] Tao S L,Zhou Y C,Lee C S,et al.High-efficiency nondoped deep-blue-emitting organic electroluminescent device[J].Chem Mater,2010,22(2):2138-2141.
[4] Liu W,Chen J X,Zheng C J,et al.Novel strategy to develop exciplex emitters for high-performance OLEDs by employing thermally activated delayed fluorescence materials[J].Adv Funct Mater,2016,26(12):2002-2008.
[5] 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.
[6] Sun M L,Jiang X,Liu W,et al.Selenophene and fluorene based narrow band gap copolymers with Eg=1.41eV for near infrared polymer light emitting diodes[J].Synthetic Met,2012,162(15/16):1406-1410.
[7] Mandado M,Gonzalez-moa M J,Mosquera.QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles[J].J Comput Chem,2007,28(1):127-136.
[8] Tanaka S,Kumagai T,Mukai T,et al.1,4-Dihydropyrrolo[3,2-b]pyrrole:the electronic structure elucidated by photoelectron spectroscopy[J].Bull Chem Soc Jpn,1987,60(6):1981-1983.
[9] Krzeszewski M,Thorsted B,Brewer J,et al.Tetraaryl-,pentaaryl-,and hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles:synthesis and optical properties[J].J Org Chem,2014,79(7):3119-3128.
[10] Balasubramanyam R K C,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].J Phys Chem C,2016,120(21):11313-11323.
基金资助
国家自然科学基金(51603088);江苏省自然科学基金(BK20150154)