浏览全部资源
扫码关注微信
1. 中山大学, 光电材料与技术国家重点实验室
2. 物理科学与工程技术学院, 广东, 广州, 510275
收稿日期:2004-08-20,
修回日期:2004-12-28,
纸质出版日期:2006-01-20
移动端阅览
宋继国, 刘彭义, 周翔, 沈培康. 迫呫吨并呫吨的快速合成及其光电性能[J]. 发光学报, 2006,27(1): 95-99
SONG Ji-guo, LIU Peng-yi, ZHOU Xiang, SHEN Pei-kang. Quick Synthesis and Properties of Peri-Xanthenoxanthene[J]. Chinese Journal of Luminescence, 2006,27(1): 95-99
用微波碳浴法
以2-萘酚为原料
快速合成了迫呫吨并呫吨.优化后的反应条件:醋酸铜(Cu(OAc)
2
)做氧化剂;Cu(OAc)
2
与2-萘酚的量的比为3:1;加热时间为210s左右。在氯仿溶液中
其吸收光谱与发射光谱呈镜面对称关系
最大发射峰波长约为445nm
且呈现较高的荧光量子效率。循环伏安法测得该化合物的最高占有分子轨道(HOMO)和最低未占有分子轨道(LUMO)分别为5.45eV
3.00eV。
We report here the quickly synthesis of peri-xanthenoxanthene using microwave carbon bath for the first time. A specific reactor is assembled to prepare the production with high yield by one step. A 100 mL glass beaker containing a mixture of 2-naphthol and cupric salt is used as reactor and covered by a watch glass. Another 250 mL glass beaker containing powder is served as a thermal bath. The reactor is placed into the bigger beaker. Thermal treatment is accomplished by dielectric loss heating of the carbon powder support using microwave irradiation. The cupric salt
reaction time and content ratio of cupric salt and 2-naphthol have been studied as reaction conditions which influence the yield of peri-xanthenoxanthene. The cupric acetate showed the higher yield than other cupric salt such as CuCl
2
CuBr
2
CuSO
4
Cu(ClO
4
)
2
Cu(NO
3
)
2
and Cu(p-OTs)
2
. The yield of peri-xanthenoxanthene increases firstly with the increase in the content ratio of Cu(OAc)
2
to 2-naphthol ranging from 1:4 to 2:1
then decreases after the content ratio over 4:1. The highest yield (86.4%) is gained at content ratio of 3:1. The 1
1'-bi-2-naphthol is the main product if the heating time less than 90 s. The main product changes to peri-xanthenoxanthene over 100 s heating time and the yield of peri-xanthenoxanthene is hardly changed at the heating time was from 150 s to 270 s. It is concluded that 1
1'-bi-2-naphthol is the inter-mediate during the synthesis process from 2-naphthol to peri-xanthenoxanthene. The absorption spectrum and photoluminescence spectrum of peri-xanthenoxanthene are symmetric. The maximum absorption and emission wavelength are 443.6 nm and 445.0 nm respectively. The quantum efficiency is 0.95 in CHCl
3
solution
indicating it is a good blue organic electroluminescent materials. The HOMO and LUMO energy levels of peri-xanthenoxanthene are determined by the cyclic voltammetry. The experimental results show that the HOMO and LUMO energy levels are 5.45 eV and 3.00 eV that means a good hole transfer ability. The product begins sublime at 238℃
however
it is stable in the air according to the thermogravimetric analysis. The differential scanning calorimetry (DSC) measurement shows that its glass transition temperature is 133℃. By considering the use of peri-xanthenoxanthene as hole transfer layer in OLED
the lifetime of these diodes would be very short since the planar molecular configuration cannot form stable amor-phous membrane.
Gustafsson G,Cao Y,Treacy G M,et al.Flexible light-emitting diodes made from soluble conducting polymers[J].Nature,1992,357:477-479.
Müller C D,Falcou A,Reckefuss N,et al.Multi-colour organic light-emitting displays by solution processing[J].Nature,2003,421:829-833.
Service R F.Organic light emitters gain longevity[J].Science,1996,273:878-880.
Sheats J R,Antoniadis H,Hueschen M,et al.Organic electroluminescent devices[J].Science,1996,273:884-888.
Dettling A,Rieker A,Speiser B.Reversible electrochemical oxidation of 2,5,8,11-tetra-tert-butyl-peri-xanthenoxanthene to its radical cation and dication[J].Tetra.Lett.,1988,29(36):4533-4534.
Inabe T,Asari T,Hasegawa H,et al.Phthalocyanine-based multi-dimensional conductors[J].Synth.Metals,2003,133-134:515-518.
Pummerer R,Prell E,Rieche A.Darstellung von binaphthylendioxyd[J].Ber.Dtsch.Chem.Ges.,1926,59:2159-2161.
Prowse W G,Arnot K I,Recka J A,et al.The quincyte pigments:fossil quinines in an Eocene clay mineral[J].Tetrahedron,1991,47(6):1095-1108.
Rieker A,Zeller N,Schurr K,et al.Vom β-naphthol abgeleitete oxyl-radikale[J].Liebigs Ann.Chem.,1966,679:691-697.
Huang C W,Li F Y,Huang Y Y.Ultrathin Films for Optics and Electronics[M].Beijing:Peking University Press,2001,158.
Wei Y J,Kang Z M,Qi X J,et al.Fluorescence spectra and fluorescence quantum yield of aurintricarboxylic acid[J].Acta Chimica Sinica (化学学报),2001,59(10):1619-1622 (in Chinese).
Wu F,Tian W J,Zhang H Y,et al.Electrochemical properties and electronic energy level structure of Os(Ⅱ) complexes[J].Chem.J.Chin.Univ.(高等学校化学学报),1998,19(10):1671-1673 (in Chinese).
Liu P Y,Xu N S,Zhao F L,et al.Preparation and photoelectric properties of ZnqCl2 thin films and devices[J].Chin.J.Lumin.(发光学报),2003,24(4):412-416 (in Chinese).
0
浏览量
111
下载量
0
CSCD
关联资源
相关文章
相关作者
相关机构