Synthesis of poly(arylenevinylene)s with fluorinated vinylene units

被引：64

作者：

Babudri, Francesco ^{[1
,2
]}

Cardone, Antonio ^{[1
]}

Farinola, Gianluca M. ^{[2
]}

Martinelli, Carmela ^{[2
]}

Mendichi, Raniero ^{[3
]}

Naso, Francesco ^{[1
,2
]}

Striccoli, Marinella ^{[4
]}

机构：

[1] CNR, ICCOM, Ist Chim Composti Organomet, I-70126 Bari, Italy

[2] Univ Bari, Dipartimento Chim, I-70126 Bari, Italy

[3] CNR, ISMAC, Ist Studio Macromol, I-20133 Milan, Italy

[4] CNR, IPCF, I-70126 Bari, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 11期

关键词：

polymers; stannanes; cross-coupling; blueshift; fluorine;

D O I：

10.1002/ejoc.200700815

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Poly(arylenevinylene) polymers bearing fluorine atoms in the vinylene units were obtained by a Stille cross-coupling reaction of (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) with diiodoaryl derivatives. The introduction of fluorine atoms on the double bond of the stannane leads to polymers with relatively high molecular weights, Furthermore, the presence of fluorinated vinylene units changes the optical properties of the polymers and shifts the emission towards the blue region of the visible spectrum. A fluorinated analogue of MEH-PPV was obtained, and it shows photoluminescence that is considerably blueshifted, also in the solid state, relative to that found for nonfluorinated MEH-PPV and to other PPVs with fluorinated double bonds. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：1977 / 1982

页数：6

共 35 条

[21] About supramolecular assemblies of π-conjugated systems [J].

Hoeben, FJM ;

Jonkheijm, P ;

Meijer, EW ;

Schenning, APHJ .

CHEMICAL REVIEWS, 2005, 105 (04) :1491-1546

[22] Spectroscopic and travelling-wave lasing characterisation of Gilch-type and Horner-type MEH-PPV [J].

Holzer, W ;

Penzkofer, A ;

Tillmann, H ;

Hörhold, HH .

SYNTHETIC METALS, 2004, 140 (2-3) :155-170

[23] A new family of highly emissive soluble poly(p-phenylene vinylene) derivatives.: A step toward fully conjugated blue-emitting poly(p-phenylene vinylenes) [J].

Hsieh, BR ;

Yu, Y ;

Forsythe, EW ;

Schaaf, GM ;

Feld, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :231-232

[24] Poly(fluorenevinylene) derivative by Gilch polymerization for light-emitting diode applications [J].

Jin, SH ;

Park, HJ ;

Kim, JY ;

Lee, K ;

Lee, SP ;

Moon, DK ;

Lee, HJ ;

Gal, YS .

MACROMOLECULES, 2002, 35 (20) :7532-7534

[25] Novel electroluminescent polymers with fluoro groups in vinylene units [J].

Jin, Y ;

Kim, J ;

Lee, S ;

Kim, JY ;

Park, SH ;

Lee, K ;

Suh, H .

MACROMOLECULES, 2004, 37 (18) :6711-6715

[26] Yellow-light-emitting fluorine-substituted PPV derivative [J].

Kang, IN ;

Shim, HK ;

Zyung, T .

CHEMISTRY OF MATERIALS, 1997, 9 (03) :746-749

[27] Synthesis and characterization of oligo(9,9-dihexyl-2,7-fluorene ethynylene)s: For application as blue light-emitting diode [J].

Lee, SH ;

Nakamura, T ;

Tsutsui, T .

ORGANIC LETTERS, 2001, 3 (13) :2005-2007

[28] Stereoselective preparation of(E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] and stereospecific synthesis of (E)-1,2-difluorostilbenes [J].

Liu, QB ;

Burton, DJ .

ORGANIC LETTERS, 2002, 4 (09) :1483-1485

[29] Versatile synthesis of various conjugated aromatic homo- and copolymers [J].

Martin, RE ;

Geneste, F ;

Chuah, BS ;

Fischmeister, C ;

Ma, YG ;

Holmes, AB ;

Riehn, R ;

Cacialli, F ;

Friend, RH .

SYNTHETIC METALS, 2001, 122 (01) :1-5

[30] Efficient blue-green light emitting poly(1,4-phenylene vinylene) copolymers [J].

Martin, RE ;

Geneste, F ;

Riehn, R ;

Chuah, BS ;

Cacialli, F ;

Friend, RH ;

Holmes, AB .

CHEMICAL COMMUNICATIONS, 2000, (04) :291-292

← 1 2 3 4 →