Synthesis and polymerization of 7-alkoxycarbonyl-7,8,8-tricyanoquinodimethanes and 7,7-bis(alkoxycarbonyl)-8,8-dicyanoquinodimethanes

Itoh, Takahito; Okuno, Hiroyuki; Hishida, Takeshi; Inokuchi, Akira; Kamei, Nobuaki; Satô, Tamotsu; Kubo, Masataka; Iwatsuki, Shouji

doi:10.1016/s0040-4020(97)00961-7

Cited by 15 publications

(14 citation statements)

References 21 publications

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“…Both the polymers are white solids, and are insoluble in most common solvents such as benzene, chloroform, dichloromethane, THF, acetone, ethyl acetate, DMF, DMSO, hexane, and methanol. 132…”

Section: Rop Of Quinodimethanesmentioning

confidence: 99%

Ring-opening polymerization by lithium catalysts: an overview

et al. 2010

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This critical review summarizes recent developments in the preparation and application of lithium catalysts/initiators such as, alkyl lithium, alkoxy lithium and bimetallic lithium compounds for ring-opening polymerization (ROP). The ROP of cyclic esters, cyclic carbonates, cyclo-silazanes, cyclo-silanes, cyclo-siloxanes, cyclo-carboxylate, cyclic phosphirene and quinodimethanes are covered in this review. The present paper emphasizes the polymerization kinetics and the control exhibited by the different types of lithium initiators/catalysts. For the cases where useful properties, such as high molecular weight, narrow PDI, or stereocontrol, have been observed, a more detailed examination of the mechanistic studies of the catalysts/initiators are provided. Furthermore, this review also focuses on the synthesis of block copolymers and graft copolymers by ROP principle. The topics covered in this review regarding lithium compounds toward ROP will be of interest to inorganic, organic and organometallic chemists, material, polymer and catalytic scientists due to its unique mode of activation as compared to transition and inner transition-metals. In addition, use of these compounds in catalysis is steadily growing, because of the complementary reactivity toward ROP as compared to other metals. Finally, some aspects and opportunities which may be of interest in the future are suggested (143 references).

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Section: Rop Of Quinodimethanesmentioning

confidence: 99%

Ring-opening polymerization by lithium catalysts: an overview

et al. 2010

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“…[2] The C(CN) 2 end groups stabilize this quinoidal structure, just as they stabilize 7,7,8,. [3] We have now extended this approach to gain access to a cumulenic quinoidal porphyrin dimer 3 (see Scheme 1). The phenomenal conjugation in this compound results in amazingly intense and red-shifted electronic absorption (l max 1080 nm, e 1 Â 10 5 m À1 cm…”

mentioning

confidence: 99%

Synthesis and Crystal Structure of a Cumulenic Quinoidal Porphyrin Dimer with Strong Electronic Absorption in the Infrared

Blake

Rees

Claridge

et al. 2000

Angew. Chem. Int. Ed.

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“…QM1 was prepared according to a previous article 9 . p ‐Methylstyrene (MeSt; Tokyo Kasei Kogyo Co., Ltd.; bp = 52–53 °C/15 mmHg), styrene (HSt; Nacalai Tesque, Inc.; bp = 44–45 °C/30 mmHg), p ‐acetoxystyrene (AcOSt; Aldrich Co.; bp = 130–131 °C/19 mmHg), p ‐chlorostyrene (ClSt; Tokyo Kasei Kogyo; bp = 74–75 °C/12 mmHg), α‐methylstyrene (αMeSt; Wako Pure Chemical Industries, Ltd.; bp = 68–69 °C/25 mmHg), trans ‐β‐methylstyrene ( trans ‐βMeSt; Tokyo Kasei Kogyo; 59–60 °C/12 mmHg), cis ‐β‐methylstyrene ( cis ‐βMeSt; Tokyo Kasei Kogyo; bp = 48–49 °C/12 mmHg), 1,1‐diphenylethylene (αPhSt; Nacalai Tesque; bp = 101–102 °C/4 mmHg), and cis ‐stilbene ( cis ‐βPhSt; Aldrich Co.; bp = 82–84 °C/0.4 mmHg) were purified by distillation under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Spontaneous reactions of electron‐accepting substituted quinodimethane with substituted styrenes: Inductive and steric effects on the formation of a zwitterionic intermediate

Mitsuda

Uno

Kubo

et al. 2005

J. Polym. Sci. A Polym. Chem.

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Spontaneous reactions of an electron-accepting substituted quinodimethane, 1-(2,2-dimethyl-1,3-dioxane-4,6-dione-5-ylidene)-4-(dicyanomethylene)-2,5-cyclohexadiene, with p-substituted, a-substituted, and b-substituted styrenes were investigated. When p-substituted styrenes were used as comonomers, no spontaneous reactions took place for styrenes with an electron-accepting p substituent such as COOMe and CN groups, and both terpolymers and cycloadducts were formed for the other p-substituted styrenes. When a-substituted and b-substituted styrenes were used as comonomers, no reactions occurred for a-and b-substituted styrenes with a bulky phenyl group, and spontaneous reactions took place for those with a smaller methyl group. The reaction products were an alternating copolymer for a-substituted styrene and both terpolymers and 5-ethylidene-2,5-dimethyl-1,3-dioxane-4,6-dione for b-substituted styrenes. The position of the methyl group in the styrenes significantly affected the product formation. This behavior in the spontaneous reactions was discussed on the basis of the ability of formation of the zwitterionic tetramethylene intermediate and its conformation, determined by polar and steric effects of the substituents in the substituted styrenes. V V C 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: [5195][5196][5197][5198][5199][5200][5201][5202][5203][5204][5205][5206] 2005

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Synthesis and polymerization of 7-alkoxycarbonyl-7,8,8-tricyanoquinodimethanes and 7,7-bis(alkoxycarbonyl)-8,8-dicyanoquinodimethanes

Cited by 15 publications

References 21 publications

Ring-opening polymerization by lithium catalysts: an overview

Ring-opening polymerization by lithium catalysts: an overview

Synthesis and Crystal Structure of a Cumulenic Quinoidal Porphyrin Dimer with Strong Electronic Absorption in the Infrared

Spontaneous reactions of electron‐accepting substituted quinodimethane with substituted styrenes: Inductive and steric effects on the formation of a zwitterionic intermediate

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