Photoinitiated polymerization of acrylates and methacrylates with decahydroacridine-1,8-dione/onium salt initiator systems

Timpe, H.‐J.; Ulrich, S.; Decker, Christian; Fouassier, Jean‐Pierre

doi:10.1021/ma00069a022

Cited by 93 publications

(47 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…With the aim of comparison, the reaction was carried out not only under microwave irradiation (Scheme 1) 2,3,4,5,6,7,8,9, Chin.…”

Section: Resultsmentioning

confidence: 99%

“…1 Among them, 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione dyes with heterocyclic structure have attracted much attention, due to their very high lasing efficience. 2,3 In virtue of the bichromophoric structure incorporating both the heterocyclic nitrogen and the carbonyl groups, these dyes have been revealed to act not only as electron donors but also electron acceptors [4][5][6] in the photoinitiated polymerization 7 of acrylates and methacrylates. They are also receiving much attention due to their likeness in properties with those of 1,4-dihydropyridines, which have similarities in structure to the biologically important compounds such as NADH and NADPH.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

One-pot Synthesis of 10-Methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives under Microwave Heating without Catalyst

et al. 2005

View full text Add to dashboard Cite

A series of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives were synthesized by one-pot reaction of aldehyde, dimedone or 1,3-cyclohexanedione and methylamine in glycol or water under microwave heating without catalyst. The method has the advantage of short routine and reaction time, high yields as well as friendly environment. And the reaction was not only suitable for aliphatic and aromatic monoaldehyde, but also for aromatic dialdehyde.Keywords aldehyde, dimedone, 1, 3-cyclohexanedione, methylamine, 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione, microwave heating IntroductionDye lasers with an electrochemical control of radiation parameters have been shown to achieve stimulated emission in a broader spectral region.1 Among them, 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione dyes with heterocyclic structure have attracted much attention, due to their very high lasing efficience. 2,3 In virtue of the bichromophoric structure incorporating both the heterocyclic nitrogen and the carbonyl groups, these dyes have been revealed to act not only as electron donors but also electron acceptors 4-6 in the photoinitiated polymerization 7 of acrylates and methacrylates. They are also receiving much attention due to their likeness in properties with those of 1,4-dihydropyridines, which have similarities in structure to the biologically important compounds such as NADH and NADPH. 9 Furthermore, their method required two step reactions and complex operation.3 Therefore, it is necessary to develop an efficient and environmentally friendly synthesis for this kind of compounds.Since Gedye in 1986 used microwave heating for organic synthesis, 10 the microwave assisted organic synthesis has been a topic of continuing interest. 11 The application of microwave heating as a non-conventional energy source to activation of reactions, has now gained extensive usage, as it could lead to shorter reaction rates, higher yields, easier work-up and short reaction time. In our previous study, 12-14 we have synthesized large amounts of heterocyclic compounds by one-pot under microwave irradiation without catalyst. Through further investigation, we found that one-pot synthesis of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones from aldehyde, dimedone or 1,3-cyclohexanedione and methylamine under microwave heating without catalyst could be successfully achieved in excellent yields and short reaction time. Herein, we would like to report this facile and efficient method, which is, to the best of our knowledge, the first one-pot synthesis of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones from cheap reagents under microwave heating without catalyst. Results and discussionWith the aim of comparison, the reaction was carried out not only under microwave irradiation (Scheme 1) 2,3,4,5,6,7,8,9, Chin.

show abstract

“…With the aim of comparison, the reaction was carried out not only under microwave irradiation (Scheme 1) 2,3,4,5,6,7,8,9, Chin.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One-pot Synthesis of 10-Methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives under Microwave Heating without Catalyst

et al. 2005

View full text Add to dashboard Cite

show abstract

“…They have been used as electron donors and electron acceptors [4][5][6] and in the photoinitiated polymerization of acrylates and methacrylates [7]. In addition to this, these compounds have long been known to be potent farmeshift mutagerns in viruses and bacteria [8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro- 1,8(2H,5H)-acridinedione-9-yl]benzene, C40H48NO4

Ahmed¹,

Haase²,

El-Saddek³

et al. 2003

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of materialA mixture of dimedone (4 mmol) and isophthalaldehyde (1 mmol) was stirred at 313 K -323 K for 10 min. in aqueous methanol until the solution became cloudy, and the reaction mixture was then allowed to stand at room temperature overnight. The solid obtained was collected by filtration and crystallized from ethanol as pale yellow crystals (36 %), mp 511 K -513 K. To a solution of the latter (5 mmol) in acetic acid (10 ml) was added ammonium acetate (11 mmol). The reaction mixture was heated under reflux for 2h, cooled and poured over crashed ice. The solid obtained was then collected and crystallized from ethanol to give 1,3-bis [3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridine dione-9-yl]benzene as pale yellow crystals (yield 48 %). DiscussionAcridine-1,8-dione dyes have been shown to have very high lasing efficiency [1,2] and are also interesting in view of the electrochemical behaviour of heterocyclic compounds [3]. They have been used as electron donors and electron acceptors [4][5][6] and in the photoinitiated polymerization of acrylates and methacrylates [7]. In addition to this, these compounds have long been known to be potent farmeshift mutagerns in viruses and bacteria [8].We report here the crystal structure of the novel 1,3-bis(acridinedione-9-yl)benzene. Bond lengths and angles of the acridine skeleton are in agreement with those of related acridine derivatives

show abstract

“…Acridine-l,8-dione dyes have been shown to have very high lasing efficiency [1,2] and are also interesting in view of the electrochemical behaviour of heterocyclic compounds [3], They have been used as electron donors and electron acceptors [4][5][6] and in the photoinitiated polymerization of acrylates and methacrylates [7]. In addition to this, these compounds have long been known to be potent farmeshift mutagerns in viruses and bacteria [8].…”

Section: Discussionmentioning

confidence: 99%

Crystalstructure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,1 0 -hexahydro-1,8 ( 2H,5H) -acridinedione-9-yl] benzene, C40H48N2O4

Ahmed

Haase

El-Saddek

et al. 2003

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Photoinitiated polymerization of acrylates and methacrylates with decahydroacridine-1,8-dione/onium salt initiator systems

Cited by 93 publications

References 3 publications

One-pot Synthesis of 10-Methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives under Microwave Heating without Catalyst

One-pot Synthesis of 10-Methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives under Microwave Heating without Catalyst

Crystal structure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro- 1,8(2H,5H)-acridinedione-9-yl]benzene, C40H48NO4

Crystalstructure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,1 0 -hexahydro-1,8 ( 2H,5H) -acridinedione-9-yl] benzene, C40H48N2O4

Contact Info

Product

Resources

About