Morpholine-2,5-dione

Martínez-Palau, Meritxell; Urpí, Lourdes; Soláns, Xavier; Puiggalı́, Jordi

doi:10.1107/s0108270106010079

Cited by 3 publications

(4 citation statements)

References 10 publications

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“…ray studies with the N-aryl compound 11 the only example located [6], while the parent dione 12 with the different 2,5-arrangement of carbonyl groups has also been reported [7]. In view of the interesting hydrogen-bonding pattern discovered for 1, it is clear that there is ample opportunity for further structural studies on such simple heterocyclic imides.…”

Section: D-h … a D-h H …mentioning

confidence: 99%

“…Perhaps the closest literature comparison is with the lactam thiomorpholine-3-one 10, in which a similar hydrogen-bonding interaction leads to simple helical chains of molecules [5]. In the corresponding tetrahydro-1,4-oxazinedione series also, there have been very few previous X-ray studies with the N-aryl compound 11 the only example located [6], while the parent dione 12 with the different 2,5-arrangement of carbonyl groups has also been reported [7].…”

Section: Bondmentioning

confidence: 99%

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Tetrahydro-1,4-thiazine-3,5-dione

Aitken

Slawin

Yeh

2018

Molbank

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Section: D-h … a D-h H …mentioning

confidence: 99%

Section: Bondmentioning

confidence: 99%

Tetrahydro-1,4-thiazine-3,5-dione

Aitken

Slawin

Yeh

2018

Molbank

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“…In present case (Figure 4b), hydrogen on C2 is substituted with R-group, while hydrogens on C1 are substituted by polymer chains. Studies from other groups have proven the planarity of the ring, when hydrogens on C1 and C2 have been substituted 41 . In order to explain the conjugation of the whole ring structure, the theory of hyperconjugation needed to be introduced.…”

Section: Fluorescence Mechanismmentioning

confidence: 99%

“…Studies from other groups have proven the planarity of the ring, when hydrogens on C1 and C2 have been substituted. 41 In order to explain the conjugation of the whole ring structure, the theory of hyperconjugation needed to be introduced. This is a well-studied phenomenon, which was rst dened by R. S. Mulliken in the late 1930s.…”

Section: Fluorescence Mechanismmentioning

confidence: 99%

Design strategies for fluorescent biodegradable polymeric biomaterials

2013

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The marriage of biodegradable polymer and fluorescent imaging has resulted in an important area of polymeric biomaterials: biodegradable fluorescent polymers. Researchers have put significant efforts on developing versatile fluorescent biomaterials due to their promising in biological/biomedical labeling, tracking, monitoring, imaging, and diagnostic applications, especially in drug delivery, tissue engineering, and cancer imaging applications. Biodegradable fluorescent polymers can function not only as implant biomaterials but also as imaging probes. Currently, there are two major classes of biodegradable polymers used as fluorescent materials. The first class is the combination of non-fluorescent biodegradable polymers and fluorescent agents such as organic dyes and quantum dots. Another class of polymers shows intrinsic photoluminescence as polymers by themselves carrying integral fluorescent chemical structures in or pendent to their polymer backbone, such as Green Fluorescent protein (GFP), and the recently developed biodegradable photoluminescent polymer (BPLP). Thus there is no need to conjugate or encapsulate additional fluorescent materials for the latter. In the present review, we will review the fluorescent biodegradable polymers with emphases on material fluorescence mechanism, design criteria for fluorescence, and their cutting-edge applications in biomedical engineering. We expect that this review will provide insightful discussion on the fluorescent biomaterial design and lead to innovations for the development of the next generation of fluorescent biomaterials and fluorescence-based biomedical technology.

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TBD‐Catalyzed Ring‐Opening Polymerization of Alkyl‐Substituted Morpholine‐2,5‐Dione Derivatives

Dirauf

Bandelli

Weber

et al. 2018

Macromol. Rapid Commun.

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In a two-step synthesis, five different alkyl-substituted morpholine-2,5-dione monomers were synthesized from the natural amino acids glycine, alanine, valine, leucine, and isoleucine. The heterocyclic compounds crystallize in a boat-like conformation and are polymerized via 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed ring-opening polymerization (ROP) in tetrahydrofuran. Well-defined polymers could be obtained from the monomers based on valine, leucine, and isoleucine at a feed ratio of M/I/TBD = 100/1/0.5. Kinetic studies of the ROP reveal that the molar masses and dispersities (Đ < 1.2) could be well controlled, as confirmed by size exclusion chromatography and H NMR spectroscopy. At conversions above 50%, the polymerization rate decreases and the dispersity slightly increases, presumably due to transesterification. Matrix-assisted laser desorption time-of-flight mass spectrometry indicates the presence of polymer chains with α-end groups derived from the initiator.

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Morpholine-2,5-dione

Cited by 3 publications

References 10 publications

Tetrahydro-1,4-thiazine-3,5-dione

Tetrahydro-1,4-thiazine-3,5-dione

Design strategies for fluorescent biodegradable polymeric biomaterials

TBD‐Catalyzed Ring‐Opening Polymerization of Alkyl‐Substituted Morpholine‐2,5‐Dione Derivatives

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