Simplified Synthesis of Spiro-Bridged Ladder-Type Poly(p-phenylene)

被引:9
作者
Wang, Baoling [1 ,2 ,3 ]
Forster, Michael [1 ,2 ]
Preis, Eduard [1 ,2 ]
Wang, Huan [3 ]
Ma, Yuguang [3 ]
Scherf, Ullrich [1 ,2 ]
机构
[1] Berg Univ Wuppertal, Macromol Chem Grp, D-42097 Wuppertal, Germany
[2] Berg Univ Wuppertal, Inst Polymer Technol, D-42097 Wuppertal, Germany
[3] Jilin Univ, State Key Lab Supramol Struct & Mat, Changchun 130012, Peoples R China
基金
美国国家科学基金会;
关键词
conjugated polymers; stabilization; synthesis; LIGHT-EMITTING-DIODES; KETONIC DEFECTS; EMISSION; POLYFLUORENE; POLYMERS; DERIVATIVES; PHOTOLUMINESCENCE; DEGRADATION; OXIDATION; OLIGOMERS;
D O I
10.1002/pola.23565
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
In this study, a simplified route to synthesize soluble, spiro-bridged ladder-type poly(p-phenylene)s (spiro-LPPP) was developed. The new, simplified synthesis route for spiro-LPPP involves two reaction steps: a single-stranded precursor polymer containing diaryloylbenzene building blocks was obtained by the Suzuki reaction, followed by a subsequent twofold cyclization cascade using methanesulfonic acid to form the target spiro-LPPP. Spiro-LPPP shows a well-defined chemical structure, high molecular weight (M-n of 17,500 g/mol with a polydispersity index of 2.0), excellent thermal stability (5% weight loss at 370 degrees C), and good solubility in common organic solvents. Spiro-LPPP emits blue light (lambda(max,em) = 455 nm) with the high solution PL quantum yield (94%). The spectral properties of spiro-LPPP in the solid state are very similar to the solution properties, thus indicating a low degree of intermolecular aggregation. After annealing a thin film of spiro-LPPP to 120 degrees C in air for 3 to 24 h, its emission spectrum is unchanged, reflecting excellent thermooxidative stability. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5137-5143, 2009
引用
收藏
页码:5137 / 5143
页数:7
相关论文
共 38 条
[1]   Synthesis and optical resolution of 9,9'-spirobifluorene-1, 1'-diol [J].
Cheng, X ;
Hou, GH ;
Xie, JH ;
Zhou, QL .
ORGANIC LETTERS, 2004, 6 (14) :2381-2383
[2]   Improved synthesis of 2,2'-dibromo-9,9'-spirobifluorene and its 2,2'-bisdonor-7,7'-bisacceptor-substituted fluorescent derivatives [J].
Chiang, CL ;
Shu, CF ;
Chen, CT .
ORGANIC LETTERS, 2005, 7 (17) :3717-3720
[3]  
CHMIL K, 1993, MAKROMOL CHEM-RAPID, V14, P217
[4]   Polyfluorenes without monoalkylfluorene defects [J].
Cho, Sung Yong ;
Grimsdale, Andrew C. ;
Jones, David J. ;
Watkins, Scott E. ;
Holmes, Andrew B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11910-+
[5]  
Fiesel R, 1998, ACTA POLYM, V49, P445, DOI 10.1002/(SICI)1521-4044(199808)49:8<445::AID-APOL445>3.3.CO
[6]  
2-D
[7]   Insight into the role of oxidation in the thermally induced green band in fluorene-based systems [J].
Grisorio, Roberto ;
Suranna, Gian Paolo ;
Mastrorilli, Piero ;
Nobile, Cosimo Francesco .
ADVANCED FUNCTIONAL MATERIALS, 2007, 17 (04) :538-548
[8]   Solubilization of regioregular and regioirregular poly(p-phenylene)s via CF3 and OCF3 substituents to generate a model for rigid-rod polymers [J].
Grob, MC ;
Feiring, AE ;
Auman, BC ;
Percec, V ;
Zhao, MY ;
Hill, DH .
MACROMOLECULES, 1996, 29 (22) :7284-7293
[9]   ELECTROLUMINESCENCE AND PHOTOLUMINESCENCE INVESTIGATIONS OF THE YELLOW EMISSION OF DEVICES BASED ON LADDER-TYPE OLIGO(PARA-PHENYLENE)S [J].
GRUNER, J ;
WITTMANN, HF ;
HAMER, PJ ;
FRIEND, RH ;
HUBER, J ;
SCHERF, U ;
MULLEN, K ;
MORATTI, SC ;
HOLMES, AB .
SYNTHETIC METALS, 1994, 67 (1-3) :181-185
[10]   BLUE-LIGHT-EMITTING DIODES BASED ON LADDER POLYMERS OF THE PPP TYPE [J].
HUBER, J ;
MULLEN, K ;
SALBECK, J ;
SCHENK, H ;
SCHERF, U ;
STEHLIN, T ;
STERN, R .
ACTA POLYMERICA, 1994, 45 (03) :244-247