One-pot two-step lipase-catalyzed synthesis of α,ω-thiophene-capped poly(ε-caprolactone) macromonomers and their use in electropolymerization

Yılmaz, Faruk; Küçük, Asuman Çelik; Özdemir, Yaprak Itır

doi:10.1007/s00289-011-0467-2

Cited by 12 publications

(8 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The conductivity, biodegradability, and biocompatibility parameters are only reported for studies which aimed use the synthesized materials for biomedical applications. 1 (Rivers et al, 2002), 2 (Guimard et al, 2009), 3 (Ding et al, 2007Huang et al, 2007Huang et al, , 2008Guo et al, 2011dGuo et al, , 2012Zhao et al, 2017), 4 (Zhao et al, 2017), 5 (Wang et al, 2015), 6 (Ding et al, 2007, 7 (Xie et al, 2015a), 8 (Huang et al, 2008), 9 (Huang et al, 2007), 10 (Huang et al, 2008, 11 (Xie et al, 2015a;Zhao et al, 2017), 12 (Mecerreyes et al, 2000(Mecerreyes et al, , 2002, 13 (Türkan et al, 2011), 14 (da Silva et al, 2018a,b, 2019, 15 (Chao et al, 2007). (Hong and Miller, 1995;Donat-Bouillud et al, 1997), the feasibility of creating the first BECP (Figure 1Ci) by using ester linkages (PLA) to achieve biodegradability and electrical conductivity based on three π-conjugated rings, a thiophene with two other pyrroles (Rivers et al, 2002).…”

Section: Electroactive and Biodegradable Oligomers For Block Copolymersmentioning

confidence: 99%

“…Recently, some of these graft copolymers based on electroactive macromonomer approach have been effectively proposed for biomedical field, mainly based on pyrrole (Domagala et al, 2014;Guo et al, 2017) aniline (Figure 1Div) (Chao et al, 2007;Peng et al, 2011) or thiophene groups, (Türkan et al, 2011) but most works are using the electroactive aniline-based oligomers previously discussed in this minireview. Although some research groups propose new synthetic routes for novel copolymers and characterize the physical chemistry properties which could be useful in biomedical applications, studies of biocompatibility are not commonplace.…”

Section: Electroactive and Biodegradable Macromonomers For Graft Copomentioning

confidence: 99%

“…Ozdemir et al (Türkan et al, 2011) proposed a similar electroactive macromonomer with PCL and thiophenecapped (ThPCLTh) (Figure 1Dii) and reported the thiophene end groups could not react and polymerize. Thus, they copolymerized it with other conducting polymers (pyrrole and thiophene monomers) and no further cell experiments were performed to investigate the biocompatibility.…”

Section: Electroactive and Biodegradable Macromonomers For Graft Copomentioning

confidence: 99%

See 2 more Smart Citations

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

Silva

Torresi

2019

Front. Mater.

View full text Add to dashboard Cite

Electroactive biomaterials are a new generation of "smart" biomaterials based on intrinsically conducting polymers (ICP). Among them, poly(3,4-ethylenedioxythiophene) (PEDOT), polypyrrole (PPy) and polyaniline (PANI) are well known conducting polymers that present excellent electrical and optical properties emerging as main candidates for potential biomedical applications. Additionally, the biodegradability of biomaterials is very useful and desirable. In this context, biodegradable polymers based on polyesters, such as poly(D,L-lactic acid) (PDLLA), polycaprolactone (PCL), and poly(glycolic acid) (PGA) appear to be promising candidates because of their good biocompatibility and, as a consequence, they have been attracting attention as sustainable alternatives for applications in medicine. Weak molecular interaction with cells, biocompatibility, biodegradability, mechanics and topography are some of the main challenges for the use of conducting polymers as biomaterials. In order to improve their own biocompatibility, the main strategies are whether by doping with specific counter ions (biodopants) or chemically modifying the monomers with different molecules. Although conventional ICPs still present low or none biodegradability, there are relatively few examples of biodegradable electroactive polymers in the literature. Recently, novel approaches have been applied to solve the problem of lack of biodegradability of conducting polymers, mainly through (1) synthesis of a modified electroactive oligomers connected via degradable ester linkages creating block copolymers and (2) synthesis of modified electroactive and biodegradable macromonomers based on polyesters used in a second step copolymerization with conductive monomers. This mini-review focuses on developing trends, challenges and summarizes the recent advances on synthesis of conducting, biodegradable and biocompatible copolymers in terms of optimizing the chemical properties to improved response toward different cells, aiming biomedical applications.

show abstract

Section: Electroactive and Biodegradable Oligomers For Block Copolymersmentioning

confidence: 99%

Section: Electroactive and Biodegradable Macromonomers For Graft Copomentioning

confidence: 99%

Section: Electroactive and Biodegradable Macromonomers For Graft Copomentioning

confidence: 99%

See 1 more Smart Citation

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

Silva

Torresi

2019

Front. Mater.

View full text Add to dashboard Cite

show abstract

“…[31] Moreover, one-pot twostep, i. e. alcohol-initiated eROP of lactones followed by a termination step, syntheses of polylactones catalyzed with Novozym®435 (commercial immobilized CAL-B) were applied in bulk media to synthesize difunctionalized poly-ω-PDL with thiol-thiol or thiol-acrylate groups [32] or α,ω-thiophene-capped poly(ɛ-caprolactone). [33] The broad substrate scope applied in eROP of lactones illustrated the enantio-, regio-and chemoselectivity of used enzymes. [60] Reported examples of the selectivity displayed by enzymes in bulk conditions are e. g. lipase PC-catalyzed ROP of racemic 3-methyl-4-oxa-6-hexanolide at 60°C, for which the apparent initial reaction rate of the (S)-isomer was seven-fold larger than that of (R)-isomer, [61] or the Novozym®435-catalyzed ROP of 4-substituted ɛ-CLs.…”

Section: Kinetics and Substrate Scope Of Erop Of Lactonesmentioning

confidence: 99%

Section: Kinetics and Substrate Scope Of Erop Of Lactonesmentioning

confidence: 99%

Enzymatic Ring‐Opening Polymerization of Lactones: Traditional Approaches and Alternative Strategies

et al. 2019

View full text Add to dashboard Cite

Biodegradable polymers such as polylactides and other polylactones and their synthesis gain progressively importance. Enzymatic ring‐opening polymerization (eROP) is the next step sustainable synthesis of polyesters, also suitable for biomedical applications due to high selectivity and lack of toxic agents. The possibility for applying diverse reaction media ranging from traditional bulk and organic media to greener alternatives such as aqueous media, ionic liquids, and supercritical fluids may allow designing alternative non‐conventional processes with less environmental footprint. Target success criteria such as high molecular weight and uniformity of polymers, and conversion of monomers have to be carefully evaluated in these diverse media. Herein we discuss the influence of different reaction media and conditions such as water content, temperature and time on the polymer sizes achieved in eROPs and various approaches to improve the molecular weight and uniformity of polymers.

show abstract

Macromonomers

Neugebauer

2016

Encyclopedia of Polymer Science and Technology

View full text Add to dashboard Cite

Macromonomers are large monomers containing repeating units and a polymerizable or functional group. Strategies such as grafting through (polymerization) and grafting to (coupling) are known as the macromonomer methods for the synthesis of functional “smart” polymers with nonlinear topologies and precisely designed properties. The variety of structures includes mono‐ and difunctional (homo‐ and heterofunctional), single‐, double‐, and triple‐tailed, star‐ and dendron‐tailed polymers. Well‐defined macromonomers are commonly applied as surface modifiers, stabilizers, compatibilizers, emulsifiers, and as building blocks of polymacromonomers, that is block and graft copolymers (molecular brushes), star copolymers (miktoarm stars), branched polymers, and networks. This articles overviews various types of macromonomers, synthetic methods for their preparation, representative examples, and the most common applications.

show abstract

One-pot two-step lipase-catalyzed synthesis of α,ω-thiophene-capped poly(ε-caprolactone) macromonomers and their use in electropolymerization

Cited by 12 publications

References 31 publications

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

Advances in Conducting, Biodegradable and Biocompatible Copolymers for Biomedical Applications

Enzymatic Ring‐Opening Polymerization of Lactones: Traditional Approaches and Alternative Strategies

Macromonomers

Contact Info

Product

Resources

About