Synthesis of mesogenic phthalocyanine-C60 donor-acceptor dyads designed for molecular heterojunction photovoltaic devices

被引：35

作者：

Geerts, Yves Henri ^{[1
]}

Debever, Olivier ^{[1
]}

Amato, Claire ^{[1
]}

Sergeyev, Sergey ^{[1
,2
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Polymeres, B-1050 Brussels, Belgium

[2] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 5卷

关键词：

donor-acceptor dyad; fullerene; liquid crystals; phthalocyanine; phthalonitrile; PHOTOINDUCED CHARGE-SEPARATION; ORGANIC SOLAR-CELLS; LOW-BAND-GAP; DISCOTIC LIQUID-CRYSTALS; FIELD-EFFECT TRANSISTORS; FULLERENE DYADS; OCTAALKOXYCARBONYL PHTHALOCYANINES; RECOMBINATION PROCESSES; COLUMNAR MESOMORPHISM; ELECTRONIC-STRUCTURE;

D O I：

10.3762/bjoc.5.49

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of phthalocyanine-C-60 dyads 2a-d was synthesized. Key steps in their synthesis are preparation of the low symmetry phthalocyanine intermediate by the statistical condensation of two phthalonitriles, and the final esterification of the fullerene derivative bearing a free COOH group. Structural characterization of the molecules in solution was performed by NMR spectroscopy, UV- vis spectroscopy and cyclic voltammetry. Preliminary studies suggest formation of liquid crystalline (LC) mesophases for some of the prepared dyads. To the best of our knowledge, this is the first example of LC phthalocyanine-C-60 dyads.

引用

页数：9

共 63 条

[21]

Huang XB, 2002, CHEM-EUR J, V8, P4179, DOI 10.1002/1521-3765(20020916)8:18<4179::AID-CHEM4179>3.0.CO

[22]

2-L

[23] Synthesis and liquid crystal properties of phthalocyanine derivatives containing both alkyl and readily oxidised phenolic substituents [J].

Humberstone, P ;

Clarkson, GJ ;

McKeown, NB ;

Treacher, KE .

JOURNAL OF MATERIALS CHEMISTRY, 1996, 6 (03) :315-322

[24] PREPARATION AND CHARACTERIZATION OF FULLEROID AND METHANOFULLERENE DERIVATIVES [J].

HUMMELEN, JC ;

KNIGHT, BW ;

LEPEQ, F ;

WUDL, F ;

YAO, J ;

WILKINS, CL .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :532-538

[25] Very high time-of-flight mobility in the columnar phases of a discotic liquid crystal [J].

Iino, H ;

Hanna, J ;

Bushby, RJ ;

Movaghar, B ;

Whitaker, BJ ;

Cook, MJ .

APPLIED PHYSICS LETTERS, 2005, 87 (13) :1-3

[26] Photoinduced electron transfer of double-bridged phthalocyanine-fullerene dyads [J].

Isosomppi, Marja ;

Tkachenko, Nikolai V. ;

Efimov, Alexander ;

Vahasalo, Heidi ;

Jukola, Johanna ;

Vainiotalo, Pirjo ;

Lemmetyinen, Helge .

CHEMICAL PHYSICS LETTERS, 2006, 430 (1-3) :36-40

[27] Polymer-fullerene bulk heterojunction solar cells [J].

Janssen, RAJ ;

Hummelen, JC ;

Saricifti, NS .

MRS BULLETIN, 2005, 30 (01) :33-36

[28] PHOTOCHEMICAL FULLEROID TO METHANOFULLERENE CONVERSION VIA THE DI-PI-METHANE (ZIMMERMAN) REARRANGEMENT [J].

JANSSEN, RAJ ;

HUMMELEN, JC ;

WUDL, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :544-545

[29] [2.2]Paracyclophane:: a pseudoconjugated spacer for long-lived electron transfer in phthalocyanine-C60 dyads [J].

Kahnt, Axel ;

Guldi, Dirk M. ;

de la Escosura, Andres ;

Martin-Diaz, M. Victoria ;

Torres, Tomas .

JOURNAL OF MATERIALS CHEMISTRY, 2008, 18 (01) :77-82

[30] Photoinduced charge-separation and charge-recombination processes of fullerene[60] dyads covalently connected with phenothiazine and its trimer [J].

Kawauchi, Hidehito ;

Suzuki, Shuichi ;

Kozaki, Masatoshi ;

Okada, Keiji ;

Islam, D. -M. Shafiqul ;

Araki, Yasuyuki ;

Ito, Osamu ;

Yamanaka, Ken-ichi .

JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (26) :5878-5884

← 1 2 3 4 5 6 7 →