The repetitive Diels-Alder reaction: A new approach to [60]fullerene maindashchain polymers

Gügel, Andreas; Belik, Pavel; Walter, Michael G.; Kraus, A.; Harth, Eva; Wagner, Manfred; Spickermann, Jochen; Müllen, Kläus

doi:10.1016/0040-4020(96)00108-1

Cited by 57 publications

(31 citation statements)

References 28 publications

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“…Even though photopolymerization was one of the very first ways to attach one fullerene to another, the method never really took on outside certain specific fields, as the polymerizations were conducted with unsubstituted fullerene in solid state and under high pressure, and resulted in unprocessable oligomers 10. Nowadays most polymeric fullerenes are achieved with “pearl necklace”11 or “pendant”12, 13 structures, with fullerene attached to a polymerizable moiety. This far the only photopolymerizations achieved with fullerene derivatives have been a photomicellization,14 photoinduced solution polymerizations,15, 16 which requires further purification procedures for the polymer to be usable, and a photo crosslinking, where fullerene attaches to a polymer 17…”

Section: Introductionmentioning

confidence: 99%

Low locoregional failure rates in selected breast cancer patients with tumor‐positive sentinel lymph nodes who do not undergo completion axillary dissection

Hwang

González-Angulo

et al. 2007

Cancer

151

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The synthesis and optimization of novel bioactive components is key to the development of antifouling marine coatings. It was recently demonstrated that medetomidine (MM) has perfect antibarnacle behavior along with good ecological properties. To investigate the applicability of MM in self‐polishing marine paints, a large set of mixtures of MM with two commercial alkyd resins (ARs) was prepared. The nature and strength of the intermolecular interaction as a function of composition in both the liquid and solid states were studied using NMR and FTIR techniques, respectively. It was found that at low concentrations MM molecules were coordinated to alkyd resin chains by hydrogen bonding. This interaction had a multidentate character (i.e., one molecule of MM interacted with several COOH species of ARs) that resulted in stronger bonding between the two compounds. However, at higher MM concentrations an ionic association between the two compounds began, which at a large MM content resulted in microphase separation. It was noted that the strong interaction between medetomidine and the alkyd resins investigated was a positive factor for the application of these compounds in self‐polishing marine paints. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 2006

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Section: Introductionmentioning

confidence: 99%

Low locoregional failure rates in selected breast cancer patients with tumor‐positive sentinel lymph nodes who do not undergo completion axillary dissection

Hwang

González-Angulo

et al. 2007

Cancer

151

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“…Work has been performed to these ends, for example via DielsAlder chemistry, 24 or by pre-modifying the sphere. However, these techniques can lead to crosslinking or be quite complex to perform.…”

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confidence: 99%

Increased thermal stabilization of polymer photovoltaic cells with oligomeric PCBM

Ramanitra

Dowland

Bregadiolli³

et al. 2016

J. Mater. Chem. C

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The first oligomerisation of phenyl-C 61 -butyric acid methyl ester (PCBM) using a facile atom transfer radical addition polymerization (ATRAP) and its exploitation for organic photovoltaic devices is described.Oligo{(phenyl-C 61 -butyric acid methyl ester)-alt-[1,4-bis(bromomethyl)-2,5-bis(octyloxy)benzene]} (OPCBMMB) shows opto-electronic properties equivalent to those of PCBM but has a higher glass transition temperature. When mixed with various band gap semiconducting polymers, OPCBMMB delivers performances similar to PCBM but with an enhanced stabilization of the bulk heterojunction in photovoltaic devices on plastic substrates under thermal stress, regardless of the degree of crystallinity of the polymer and without changing opto-electronic properties.

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“…It is im por tant to note that due to the ex is tence of a sulfolene group in ad ducts (20, 22, 25, and 27), one can still add in an other func tion al ity through a sec ond stage Diels-Alder re ac tion. 10 Thus, benzodisultine is use ful for the syn the sis of multifunctional polycyclic compounds.…”

Section: Re Sults and Discussionmentioning

confidence: 99%

The Synthesis of Naphthosultine and Benzodisultines and Their Pyrolysis with Dienophiles: Studies on o‐Naphthoquinodimethane and Bis‐o‐Quinodimethane

Liu

Chung

2002

J Chinese Chemical Soc

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Sealed tube re ac tions of the naphthosultine 8 with a se ries of elec tron-deficient dienophiles (fumaronitrile, N-phenylmaleimide, dimethyl fumarate, and dimethyl acetylenedicarboxylate) in to lu ene at 180 °C gave cor re spond ing 1:1 cycloadducts 11-14 in var i ous amounts along with re ar ranged naphthosulfolene 7 in 67-95% yields. The re ac tion of 1,2,4,5-tetra(bromomethyl)ben zene with Rongalite (so dium form al de hyde sulfoxylate) and tetrabutylammonium bro mide in DMF gave benzodisultines 17 and 18 in a com bined yield of 56%. Sealed tube re ac tions of benzodisultines 17 and 18 with a se ries of dienophiles in xylene at 200 C gave cor re spond ing 1:1 and 1:2 cycloadducts 20-27. The re sults sug gested that ther mal ex tru sion of sul fur di ox ide from these sultines led to ei ther o-naphthoquinodimethane 6 (from 8) or bis-o-quinodimethane 19 (from 17 and 18); sub se quent trap ping of these re ac tive in ter me di ates by dienophiles and SO2 gave var i ous 1:1 and 1:2 Diels-Alder ad ducts in mod est to ex cel lent yields. IN TRO DUC TIONMuch at ten tion has been fo cused on the syn the sis of polycyclic com pounds us ing o-quinodimethane (o-QDM) 1 and its an a logues, and nu mer ous meth ods for the gen er a tion of the o-QDM in ter me di ates have been de vel oped. have been shown to lead to the o-QDM in ter me di ates.In a pi o neer ing work by Cava and co work ers, 6a the naphtho an a logue of o-QDM 6 was gen er ated us ing SO2 extru sion from sulfolene 7; how ever, a re ac tion tem per a ture of 300 C was re quired! The naphthoquinodimethane 6 was later re ported by Wirz et. al. us ing a diazene-precursor, 6b but the diazene com pound was un sta ble and had to be kept un der -40 C. Fur ther more, an in trac ta ble mix ture of prod ucts was ob tained in deaerated so lu tion of the diazene com pound.Thus, find ing an easy, high-yield method for gen er at ing naphthoquinodimethane 6 and a fur ther ex ten sion to bis-o-QDM are of par tic u lar in ter ests. Re cently we de scribed 7 the gen er a tion of a se ries of heteroaromatic o-QDMs, by ther mal ex tru sion of SO2 from cor re spond ing sultines, and ex plored their ap pli ca tion in Diels-Alder re ac tions with dienophiles in clud ing [60]fullerene. The ad van tages of us ing sultines are (1) their thermolysis oc curs at a much lower tem per a ture than that of cor re spond ing sulfolenes, 7-8 and (2) they are usu ally sta ble above room tem per a ture. We re port here our work on the syn the sis of naphthosultine 8 and benzodisultines 17 and 18 and their ap pli ca tions in Diels-Alder re ac tions with alkenes and al kynes. RE SULTS AND DIS CUS SIONNaphthosultine 8 is readily syn the sized in three steps from 2,3-naphthalene-dicarboxylate with an over all yield of 42%, as shown in Scheme I. The 2,3-di(bromomethyl)naphtha lene 10 was ob tained in 70% yield by bromination of the naphthodiol 9, and the diol was ob tained in 96% yield from a lith ium alu mi num hy dride re duc tion of the dicarboxylate. Sub se quent treat ment of the dibromide 10 wi...

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The repetitive Diels-Alder reaction: A new approach to [60]fullerene maindashchain polymers

Cited by 57 publications

References 28 publications

Low locoregional failure rates in selected breast cancer patients with tumor‐positive sentinel lymph nodes who do not undergo completion axillary dissection

Low locoregional failure rates in selected breast cancer patients with tumor‐positive sentinel lymph nodes who do not undergo completion axillary dissection

Increased thermal stabilization of polymer photovoltaic cells with oligomeric PCBM

The Synthesis of Naphthosultine and Benzodisultines and Their Pyrolysis with Dienophiles: Studies on o‐Naphthoquinodimethane and Bis‐o‐Quinodimethane

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