A novel polycarbonate for high temperature electro-optics via azo bisphenol amines accessed by Ullmann coupling

Suresh, S.; Gulotty, Robert; Bales, Stephen; Inbasekaran, M.; Chartier, Mark A.; Cummins, Clark H.; Smith, Dennis W.

doi:10.1016/s0032-3861(03)00529-9

Cited by 26 publications

(21 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The PET film had clear birefringence, as showed in Figure 8, while the films of 3a and 3d hardly showed the birefringence, in accordance with the reports on other polymers containing 9,9-diarylfluorenes. [1][2][3][4][5][6][7][8][9] Degree of retardation at 590 nm in 3d (thickness: 250 mm) was less than 3.28 nm in undrawn state, 53 and the birefringence value was remarkably low (less than 1:3 Â 10 À5 ). In the drawn film of 3d (drawn ratio is 2.0), the birefringence value was À8:9 Â 10 À4 , and the stress optical coefficient was very low (À0:15 GPa À1 ).…”

Section: Birefringencementioning

confidence: 99%

“…Such low birefringence should be attributed to the optical anisotropy decreasing effect of the cardo structure of the 9,9-diarylfluorene moiety placed in the main chain as mentioned. [1][2][3][4][5][6][7][8][9] The fluorene moiety and the two phenyl groups at the C9-position occupy different planes and are crossed at the precise angle that renders the structure most stable. Placing the aromatic rings on the different planes might disturb their one-directional folding, and thereby the optical anisotropy of the F-PEs disappears.…”

Section: Birefringencementioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] Such optical property is caused by the presence of many aromatic rings in the 9,9-diarylfluorene moiety which occupy the different planes to disturb the interchromophore packing, effectively decreasing the optical anisotropy. Meanwhile, such polymers also display excellent filler-dispersing ability [10][11][12] in addition to their high thermal stability, [13][14][15][16] high solubility, [17][18][19] and so on.…”

mentioning

confidence: 99%

See 2 more Smart Citations

9,9-Diarylfluorene-Based Poly(alkyl aryl ether)s: Synthesis and Property

et al. 2009

View full text Add to dashboard Cite

Polyethers possessing 9,9-diarylfluorene moieties in the main chain (F-PEs 3) were synthesized in 85-99% yields by the polycondensation of 9,9-bis(hydroxyaryl)fluorenes with alkyl ditosylates in the presence of cesium carbonate. Molecular weight of the F-PEs was dependent on the structure of the ditosylate 1; cyclohexyl-1,4-dimethylene (1a), 1,2-ethylene (1b), 1,3-trimethylene (1c), and 1,6-hexamethylene (1d). Higher molecular weight F-PEs (M n 32000-60000, M w 74000-160000) was obtained when longer alkyl chain ditosylates (1a and 1d) were used. The F-PEs showed good solubility toward various organic solvents such as toluene and high 5% weight loss temperature (T d5 : 424-447 C). The glass transition temperature of F-PEs (T g ) was ranging from 147 to 220 C. No melting point (T m ) was observed. F-PEs showed high water-resistance. The transmittance of F-PEs in film state (thickness: 21-32 mm) reached over 90% in the visible region. The F-PEs exhibited high refractive indices in a range of 1.62-1.66 at 590 nm in addition to sufficiently low birefringence values, probably due to the cardo structure of the fluorene moiety placed in the main chain. The structural dependence of dispersing ability to fullerene C 60 was investigated.KEY WORDS: Cardo Structure / Polyether / Refractive Index / Birefringence / Solubility / Thermal Stability / Processability / 9,9-Diarylfluorene-based polymers attract much attention due to the unique characteristics originated from the ''cardo'' structure as characterized often by the high refractive index and low birefringence.1-9 Such optical property is caused by the presence of many aromatic rings in the 9,9-diarylfluorene moiety which occupy the different planes to disturb the interchromophore packing, effectively decreasing the optical anisotropy. Meanwhile, such polymers also display excellent filler-dispersing ability [10][11][12] in addition to their high thermal stability, [13][14][15][16] high solubility, [17][18][19] and so on. [20][21][22][23][24][25] We have recently reported the special -interaction of the 9,9-diarylfluorene moiety in the matrix polymers toward -face of the carbon fillers.26 Although many polymers possessing 9,9-diarylfluorene moieties in the main chain have been developed to date, there is no study on polyethers. Polyethers are an important class of high performance engineering thermoplastics with a favorable combination of physical, mechanical, and chemical properties, other than processability, [31][32][33][34][35][36][37][38][39][40][41] and are easily synthesized usually by the polycondensation of diols and ditopic electrophiles. Polyethers with good optical and physical properties can be obtained, 42,43 if saturated alkyl group is introduced into the polymer main chain in addition to 9,9-diarylfluorene moiety, because the alkyl group often shows no optical anisotropy.Herein, we wish to disclose the synthesis and property of poly(alkyl aryl ether)s (F-PEs) containing 9,9-diarylfluorene moiety in the main chain, with emphasis on the effect of alkyl chai...

show abstract

Section: Birefringencementioning

confidence: 99%

Section: Birefringencementioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

9,9-Diarylfluorene-Based Poly(alkyl aryl ether)s: Synthesis and Property

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Other research groups as well as our own are currently studying PFCB aryl ether polymers for possible EO applications. [120][121][122][123][124][125][126][127][128][129] Our group is currently investigating PFCB aryl ether polymers functionalized with a series of triaryl amino-based chromophores that possess unprecedented hyperpolarizability values (20,000 3 10 À30 esu measured at 1.6 lm). [130][131][132] Liquid Crystalline Polymers Liquid crystalline (LC) polymers are used as displays in electro-optic devices and require interfacial ordering as well as thermal stability; fluoropolymers, in particular, are quite advanced in this respective area.…”

Section: Electro-opticsmentioning

confidence: 99%

Science and technology of perfluorocyclobutyl aryl ether polymers

Iacono

Budy

Jin

et al. 2007

J. Polym. Sci. A Polym. Chem.

103

View full text Add to dashboard Cite

show abstract

“…产率不高而且反应条件比较苛刻, 大都需要在高温 [3] 、强碱 [4] 的条件下且时间反应长, 这使得 Ullmann 应用受到很大限制. 不过一些新的技术和方法已被应用于此反应, 例如采用超声辅助 [5] 或采用选择性更强的试剂 [6] , 然而这些方法的产率仍然不高.…”

unclassified

Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

Xiao¹,

Zhu²,

Mu³

et al. 2013

Chin. J. Org. Chem.

View full text Add to dashboard Cite

The Ullmann reaction has been extensively applied in the synthesis of organic intermediates, especially in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond. It has been demonstrated that microwave irradiation can obviously accelerate the Ullmann reaction and improve the yields, so the application of microwave in the Ullmann reaction has caught increasing attention in recent years. The application of microwave in the Ullmann reaction and the progresses in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond are reviewed in this paper. Keywords Ullmann reaction; microwave; synthesis; review 经典的 Ullmann 反应是指以两芳基卤代物为原料, 在铜粉催化作用下, 生成二芳基化合物 2 (Eq. 1)的反应. 不过, 该反应可以采用不同的过渡金属进行催化 [1] . 尽管 Ullmann 反应的应用广泛, 但是该类反应一般

show abstract

A novel polycarbonate for high temperature electro-optics via azo bisphenol amines accessed by Ullmann coupling

Cited by 26 publications

References 21 publications

9,9-Diarylfluorene-Based Poly(alkyl aryl ether)s: Synthesis and Property

9,9-Diarylfluorene-Based Poly(alkyl aryl ether)s: Synthesis and Property

Science and technology of perfluorocyclobutyl aryl ether polymers

Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

Contact Info

Product

Resources

About