Malte Winnacker

Technische Universität München | TUM · WACKER-Lehrstuhl für Makromolekulare Chemie

Polyamides (PA) are among the most essential and versatile polymers due to their outstanding characteristics, e.g., high chemical resistance and temperature stability. Furthermore, nature‐derived monomers can introduce hard‐to‐synthesize structures into the PAs for unique polymer properties. Pinene, as one of the most abundant terpenes in nature an...

Polyamides are very important polymers, with applications from commodities up to high‐performance materials for, for example, fibers or for the biomedical sector. Nowadays, still most of them are synthesized from fossil resources. With regards to sustainability and bioeconomy, and especially regarding the new structures and properties that can thus...

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Front Cover: Article 2200185 by Paul N. Stockmann, Malte Winnacker, and co‐workers highlights the scalable synthetic route to the novel monomer limonene lactam and its polymer limonene polyamide. The lime peel represents not only the bio‐based but also non‐food based source of the monomer. Subsequent ring‐opening polymerization gives access to a su...

The preparation of sustainable polymers from renewable resources is a main task in modern polymer and materials chemistry. For this, terpenes, that have many functions in nature, are very important building blocks, e.g., due to their abundance, availability, structural diversity, and functionalities. Accordingly, many approaches have been and are c...

The cover feature image shows a depiction of cars (representing different substrates) being directed in different paths at a junction and illustrates how the OSSO Chromium catalyst can produce cyclic carbonates or polycarbonate depending on the type of substrate and on the reaction conditions. More information can be found in the Research Article b...

In this work; the synthesis of the terpene‐based limonene lactam prepared from limonene epoxide is presented; as well as its subsequent ring‐opening polymerization (ROP) to novel polyamides. Sustainable; biobased materials are gaining interest as replacement of conventional; petroleum‐based materials; and even more important; as materials with enha...

In this work, four new mononuclear Cr(III) complexes (2–5) bearing bis‐thioether‐diphenolate, [OSSO]‐type ligands, were synthesized and characterized. These complexes in combination with bis(triphenylphosphine)iminium chloride (PPNCl) promoted the coupling of CO2 with epoxides. Depending on the type of substrate and the conditions, the reaction res...

Polyamides are very important polymers for a wide range of applications. In the context of Green Chemistry and the development of sustainable polymers from renewable resources, many polyamides have meanwhile been developed that are derived from natural building blocks. In addition to sustainability, biobased polyamides can have special structures a...

The growing environmental pollution and the expected depleting of fossil resources have sparked interest in recent years for polymers obtained from monomers originating from renewable sources. Furthermore, nature can provide a variety of building blocks with special structural features (e. g. side groups or stereo‐elements) that cannot be obtained...

Front Cover: In article number 2100065 by Magdalena Maria Kleybolte and Malte Winnacker, the synthesis of β-pinene-based polyesteramides and their monomers is investigated and significantly improved. Thus, further optimization and analysis of the synthesis of β-pinene lactam as well as its copolymerization with ε-caprolactone represents a significa...

Terpene-based polyesteramides (PEAs) are sustainable and have a variety of favorable properties, making them suitable for a wide range of applications and for contribution to a much more sustainable polymer industry. This work focuses on the synthesis of the lactam from β-pinene and its copolymerization with ε-caprolactone. An important step in syn...

Soluble heterocomplexes consisting of sodium hydride in combination with trialkylaluminum derivatives have been used as anionic initiating systems at 100 °C in toluene for convenient homo-, co- and ter-polymerization of myrcene with styrene and isoprene. In this way it has been possible to obtain elastomeric materials in a wide range of composition...

Sustainable lactams, which are derived from terpenes, are used for the synthesis of different novel copolymers via ring‐opening polymerization. Different conditions are tested and the incorporation of the different monomers into the polymers is elucidated. This gives access to a variety of new polymer structures and their application range is thus...

The use of renewable feedstock is one of the twelve key principles of sustainable chemistry. Unfortunately, bio-based compounds often suffer from high production cost and low performance. To fully tap the potential of natural compounds it is important to utilize their functionalities that could make them superior compared to fossil-based resources....

Polyhydroxyalkanoates (PHAs) are microbial biopolymers (polyesters) that have a wide range of functions and applications. They serve in nature mainly as carbon and energy storage materials for a variety of microorganisms. In past decades, their utilization has attracted much attention, from commodities and degradable plastics to specialty performan...

Back Cover: (+)‐3‐Carene and α‐pinene are abundant monoterpenes from wood and valuable biogenic resources for substituted lactams. These lactams can be used for the production of new bio‐polyamides with surprising and promising properties. In article number 1800903, Volker Sieber and co‐workers observe a high‐performance glass transition temperatur...

In addition to their established usage in textiles, commodities, and automotives, classical polyamides (nylons) are recently becoming increasingly interesting for applications in (bio)medicine. This fact relies on many prosperous properties of these polymers, which are toughness, resistance, biocompatibility, low immunogenicity, tunable biodegradab...

The synthesis and polymerization of two β‐lactams and two ε‐lactams derived from the terpenes α‐pinene and (+)‐3‐carene are reported. The new biopolymers can be considered as polyamide 2 (PA2) and polyamide 6 (PA6)‐types with aliphatic stereoregular side chains, which lead to remarkable new properties. The macromolecules are investigated by gel per...

Pinenes ‐ a group of monoterpenes containing a double bond ‐ are very suitable renewable building blocks for a variety of sustainable polymers and materials. Their abundance from mainly non‐edible parts of plants as well as the feasibility to isolate them render these compounds unique amongst the variety of biomass that is utilizable for novel mate...

Pinenes ‐ a group of monoterpenes containing a double bond ‐ are very suitable renewable building blocks for a variety of sustainable polymers and materials. Their abundance from mainly non‐edible parts of plants as well as the feasibility to isolate them render these compounds unique amongst the variety of biomass that is utilizable for novel mate...

Silicon nanocrystals (SiNCs) are abundant and exhibit exquisitely tailorable optoelectronic properties. The incorporation of SiNCs into highly porous and lightweight substrates such as aerogels leads to hybrid materials possessing the attractive features of both materials. This study describes the covalent deposition of SiNCs on and intercalation i...

A sustainable lactam, which is derived from the renewable terpene β-pinene, is converted to polyamides via a convenient anionic polymerization, which can be easily handled without the use of a...

At the interface of materials science and synthetic biology, several concepts were recently developed for the production of functional materials by living cells. Selected recent strategies for this are highlighted...

Among the variety of polymeric biomaterials, polyesters have a significant position, e.g. due to their biocompatibility and (tunable) biodegradability. In addition to their established and “pristine” use as e.g. implants or sutures, the introduction of specific functional biomolecules onto polyesters has been gaining increasing attention within the...

Among the variety of SiNC functionalization methods, radical initiated grafting is very promising due to its straightforward nature and low propensity to form surface oligomers. In the present study, we employed in-situ IR spectroscopy in combination with visible light transmittance measurements to investigate the radical induced grafting process o...

Synthetic polyamides (nylons) are very important polymers with applications in many fields, and recently their use in biology and medicine is becoming more and more important. Different recent concepts and strategies for the functionalization and applications of nylons as biomaterials are summarized in this article, with a focus on their utilizatio...

A convenient synthesis of sustainable polyamides, which contain side groups and stereocenters, starting from the biobased small terpene β-pinene is reported. The polyamides, which are obtained via the pinene-based lactam via ring-opening polymerization, show excellent thermal properties, rendering this approach very interesting for the utilization...

Poly(ester amide)s (PEAs) are very important synthetic polymers with applications in many fields. The combination of the thermal and mechanical properties of polyamides with the biocompatibility and biodegradability of polyesters affords biomaterials of great interest especially for tissue engineering and drug delivery. Recent advances are elucidat...

Subjecting polymers to elevated temperatures as well as extended exposure times can significantly increase the melt viscosity and prevent impregnation progress of carbon fiber reinforced thermoplastics (CFRTP). In this study, a polyamide 6 (PA6) and a copolyamide (PA10T/X) were subjected to repeated heating cycles (thermal cycling) derived from CFR...

Copolymers of polyhydroxyalkanoates (PHAs) and polyethylene glycols (PEGs) have gained high significance for biological and medical applications within the past years. PHAs are natural biopolymers (hydrophobic biopolyesters), which can be produced microbially and also synthetically, and PEGs are biocompatible hydrophilic polyethers, which are frequ...

Polyamides represent a very important class of polymers for a wide range of applications. After establishing in the 1930s with Nylon and Perlon, their impact on many branches has been continuously growing. In the context of developing sustainable polymers from renewable resources, many polyamides have meanwhile been described, which are based on na...

Back Cover: Sustainable polyamides with side groups and stereocenters are synthesized starting from L-menthone. This terpenoid ketone is transformed in a one-step synthesis into a chiral lactam, which is then polymerized via ring-opening polymerization (ROP). The beneficial properties of these polymers are thus introduced via the structure and chir...

Polyamides are very important polymers that find applications from commodities up to the automotive and biomedical sectors, and their impact is continuously growing. The synthesis of structurally significant, chiral, and sustainable polyamides is described via a new, convenient, and solvent-free anionic polymerization of a biobased ε-lactam, which...

The heterogeneous nature of β-butyrolactone (BL) polymerization towards tactic poly(3-hydroxybutyrate) (PHB) in the presence of chromium(III) salphen (salphen=N,N′-disalicylidene-o-phenylenediamine) complexes is supported by a number of experimental observations. Depending on the substitution pattern, initially soluble chromium(III) salphen chlorid...

Two regioisomeric lactams, which are derived from terpenoid ketone (-)-menthone in two steps, are oligomerized in an easy acid-induced procedure to obtain oligoamides that contain alkyl groups and stereocenters; for this, a nucleophilic oligomerization via a non-ionic propagating site (neutral conditions) and a polycondensation are also possible. F...

The functionalization and polymerization of biobased monocyclic terpenes and their derivatives for the synthesis of sustainable polymers is described, especially in view of the synthetic routes and properties of the obtained macromolecular architectures. Comparison of these procedures and the obtained materials with "classical" oil-based approaches...

Cooperative catalysis, where two or more factors are responsible for a polymerization reaction to occur, has been proven to have a huge impact in the past decade and is used for many of polymerization reactions. In this chapter we focus on select examples where these systems are applied for the polymerization of lactide and other cyclic esters, the...

Living organisms protect the genome against external influences by recognizing and repairing damaged DNA. A common source of gene mutation is the oxidized guanine, which undergoes base excision repair through cleavage of the glycosidic bond between the ribose and the nucleobase of the lesion. We unravel the repair mechanism utilized by bacterial gl...

In the context of novel sustainable and structurally significant building blocks for polymer science, the synthetic routes are described to new oligoamide structures based on the terpenoid ketone (-)-menthone. The basic concept is an oxime formation of this cyclic ketone followed by the Beckmann rearrangement, resulting in the corresponding lactams...

We describe in this Minireview the synthesis, properties, and applications of artificial genetic sets built from base pairs that are larger than the natural Watson-Crick architecture. Such designed systems are being explored by several research groups to investigate basic chemical questions regarding the functions of the genetic information storage...

Wir beschreiben in diesem Kurzaufsatz die Synthese, Eigenschaften und Anwendungen von künstlichen genetischen Systemen, die aus Basenpaaren bestehen, die länger sind als die Basen der natürlichen Watson‐Crick‐Architektur. Derartige Systeme werden von mehreren Arbeitsgruppen untersucht, um fundamentale chemische Fragen bezüglich der Funktion der gen...

Finding DNA repair factors: A comparative study with DNA probes containing 8-oxodG and bearing different photo-crosslinking moieties found that a triethyleneglycol-trifluoromethyl-phenyldiazirine system was excellent for the labeling of DNA repair factors. This probe was used for the activity-based and selective labeling of different DNA repair fac...

An investigation of the precise interactions between damaged DNA and DNA repair enzymes is required in order to understand the lesion recognition step, which is one of the most fundamental processes in DNA repair. Most recently, photoaffinity labeling approaches have enabled the analysis of even transient protein-DNA interactions. Here we report th...

An efficient and convenient one-pot procedure for the synthesis of enantiomerically pure 2-(hydroxymethyl)morpholines with a widely variable substitution pattern was developed. Addition of chiral beta-amino alcohols to (S)- or (R)-epichlorohydrin in the presence of LiClO4 afforded the corresponding chloro alcohols, which were treated with NaOMe to...