Vilsmeier-Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors

被引：6

作者：

Fujioka, Atsushi ^{[1
]}

Kubo, Takashi ^{[1
]}

Watanabe, Miho ^{[1
]}

Ueda, Masafumi ^{[1
]}

Miyamoto, Hisakazu ^{[1
,3
]}

Misaki, Yohji ^{[1
,2
]}

机构：

[1] Ehime Univ, Grad Sch Sci & Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan

[2] Kyoto Univ, Elements Strategy Initiat Catalysts & Batteries E, Kyoto 6158520, Japan

[3] Kurume Coll, Natl Inst Technol, Dept Gen Educ Sci, Kurume, Fukuoka 8308555, Japan

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 06期

基金：

日本学术振兴会;

关键词：

tetrathiafulvalene; redox; cyclic voltammetry; Vilsmeier-Haack reaction; heterocycles; POSITIVE ELECTRODE MATERIAL; ANALOGS; SYSTEMS;

D O I：

10.1055/s-0035-1560400

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Vilsmeier-Haack type formylations on various 6-aryl-1,4-dithiafulvenes were examined. The furyl derivatives on treatment with an excess of POCl3 in DMF at room temperature mainly afforded dialdehydes substituted at the 6-position and the furan ring, while the thienyl derivatives and the phenyl derivatives mainly gave monoformylated derivatives substituted at the 6-position. The obtained mono- and dialdehydes were converted into monoaryl-substituted 2,2-ethanediylidene-bis(1,3-dithiole) derivatives and heteroaromatic ring-inserted [3]dendralene derivatives with triple 1,3-dithiol-2-ylidenes and their TTF-fused analogues. Electrochemical properties of the new -electron donors were also investigated by cyclic voltammetry.

引用

页码：845 / 854

页数：10

共 20 条

[1] SYNTHESIS OF 1,4-DITHIAFULVENES AND 1,4-DITHIAFULVALENES BY CARBONYL OLEFINATION USING 2-DIMETHOXYPHOSPHINYL-1,3-BENZODITHIOLE [J].

AKIBA, KY ;

ISHIKAWA, K ;

INAMOTO, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (09) :2674-2683

[2] 2,5-BIS(1,4-DITHIAFULVEN-6-YL) FURANS, THIOPHENES AND N-METHYL PYRROLES AS EXTENDED ANALOGS OF TETRATHIAFULVALENE [J].

BENAHMEDGASMI, AS ;

FRERE, P ;

GARRIGUES, B ;

GORGUES, A ;

JUBAULT, M ;

CARLIER, R ;

TEXIER, F .

TETRAHEDRON LETTERS, 1992, 33 (43) :6457-6460

[3] Tetrathiafulvalene (TTF) derivatives: key building-blocks for switchable processes [J].

Canevet, David ;

Salle, Marc ;

Zhang, Guanxin ;

Zhang, Deqing ;

Zhu, Daoben .

CHEMICAL COMMUNICATIONS, 2009, (17) :2245-2269

[4] Salts of extended tetrathiafulvalene analogues:: relationships between molecular structure, electrochemical properties and solid state organisation [J].

Frère, P ;

Skabara, PJ .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (01) :69-98

[5] Orbital analysis of TTF molecules adsorbed on the Au surface [J].

Fueno, H. ;

Hayashi, M. ;

Nin, K. ;

Kubo, A. ;

Misaki, Y. ;

Tanaka, K. .

CURRENT APPLIED PHYSICS, 2006, 6 (05) :939-942

[6] NEW EXTENDED PI-ELECTRON DONORS - TETRATHIAFULVALENE SYSTEMS WITH HETEROCYCLIC SPACER GROUPS [J].

HANSEN, TK ;

LAKSHMIKANTHAM, MV ;

CAVA, MP ;

NIZIURSKIMANN, RE ;

JENSEN, F ;

BECHER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5035-5039

[7] Syntheses and properties of thiophene-inserted [3]dendralenes with redox-active 1,3-dithiol-2-ylidene units [J].

Hasegawa, Masashi ;

Fujioka, Atsushi ;

Kubo, Takashi ;

Honda, Tomohito ;

Miyamoto, Hisakazu ;

Misaki, Yohji .

CHEMISTRY LETTERS, 2008, 37 (04) :474-475

[8] A new synthetic route to TTF-vinylogues [J].

Imakubo, T ;

Iijima, T ;

Kobayashi, K ;

Kato, R .

SYNTHETIC METALS, 2001, 120 (1-3) :899-900

[9] A pentakis-fused tetrathiafulvalene system extended by cyclohexene-1,4-diylidenes: a new positive electrode material for rechargeable batteries utilizing ten electron redox [J].

Kato, Minami ;

Senoo, Ken-ichiro ;

Yao, Masaru ;

Misaki, Yohji .

JOURNAL OF MATERIALS CHEMISTRY A, 2014, 2 (19) :6747-6754

[10] A Tris-fused Tetrathiafulvalene Extended with Cyclohexene-1,4-diylidene: A New Positive Electrode Material for Organic Rechargeable Batteries [J].

Kato, Minami ;

Ogi, Daisuke ;

Yao, Masaru ;

Misaki, Yohji .

CHEMISTRY LETTERS, 2013, 42 (12) :1556-1558

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