Multidentate Polysarcosine-Based Ligands for Water-Soluble Quantum Dots

Fokina, Ana; Klinker, Kristina; Braun, Lydia; Jeong, Byeong Guk; Bae, Wan Ki; Barz, Matthias; Zentel, Rudolf

doi:10.1021/acs.macromol.6b00582

Cited by 49 publications

(45 citation statements)

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“…Therefore, we expanded 1,3-dipolar cycloaddition to azides 2 and 3 bearing two and three lipoic acid residues, respectively. 20 Consequently, the resulting polymers P2b and P2c were equipped with tetra-and hexadentate anchor groups, respectively, and the successful incorporation of the respective end groups was verified by 1 …”

Section: Resultsmentioning

confidence: 96%

“…Azides 1-5 (an illustration of compounds 1-5 can be found in the Supplementary Information (SI), Figure S1) and pentafluorophenyl 4-vinylbenzoate (PFP4VB) were synthesized according to literature procedures. [20][21][22] Syntheses of ethynyl-terminated and aldehyde-terminated P3HT were conducted following modifications of established literature procedures. 23,24 1 H, 19 F and 13 C NMR (nuclear magnetic resonance) spectra were acquired on a Bruker ARX 400 spectrometer at a Lamor frequency of 400, 376 and 101 MHz, respectively.…”

Section: Materials and Characterizationmentioning

confidence: 99%

“…20 As the device performance strongly depends on the functional group interacting with the inorganic nanoparticles, the ability to incorporate different functional groups following the same polymer synthesis approach is of special interest for studies with the aim to investigate the influence of various functional groups on the device performance.…”

Section: Introductionmentioning

confidence: 99%

“…7,19 Therefore, we incorporated both, mono-as well as multidentate anchor groups with varying functionalities (i.e., catechol, lipoic acid, amine and trithiocarbonate). 20 As the device performance strongly depends on the functional group interacting with the inorganic nanoparticles, the ability to incorporate different functional groups following the same polymer synthesis approach is of special interest for studies with the aim to investigate the influence of various functional groups on the device performance. 14 Finally, P3HT polymer chains modified with amine and disulfide functionalities were tested as anchor groups for chalcogenide nanoparticles, while TiO 2 nanoparticles have been functionalized with P3HT carrying catechol anchor groups.…”

Section: Introductionmentioning

confidence: 99%

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Functionalization of P3HT with Various Mono- and Multidentate Anchor Groups

Menk¹,

Fokina²,

Oschmann³

et al. 2017

J. Braz. Chem. Soc.

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Due to its favorable optoelectronic properties and the accessibility via Grignard metathesis (GRIM) polymerization, poly(3-hexylthiophene) (P3HT) is one of the most applied conjugated polymers. The 'living' nature of GRIM polymerization enables the modification of the polymer and the installation of desired properties. In the present study, two versatile approaches for the synthesis of anchor group-modified P3HT have been developed, which enable the functionalization of various inorganic nanoparticles. Depending on the polymerization conditions, mono-and bifunctional ethynyl-terminated P3HT or solely monofunctionalized aldehyde-terminated P3HT was synthesized. Afterwards, the quantitative introduction of amine, mono-and multidentate disulfide and catechol anchor groups was performed by copper-catalyzed 1,3-dipolar cycloaddition or via imine formation reactions. The influence of the polymeric ligand structure on the functionalization of nanoparticles was then investigated for CdSe@ZnS quantum dots and TiO 2 nanorods by transmission electron microscopy (TEM) and infrared (IR) spectroscopy. Keywords: click chemistry, conjugated polymers, P3HT, GRIM, hybrid nanocomposites IntroductionThe design of conjugated polymers with favorable optoelectronic properties has been the subject of research for several decades. Early on, the application of these organic semiconductors in organic solar cells, light-emitting diodes, optical waveguides and lasers has been envisioned and tested.1 Besides ring-opening metathesis polymerization (ROMP) and cyclopolymerization, Grignard metathesis (GRIM) polymerization represents one of the few 'living' polymerization techniques capable of synthesizing conjugated polymers.2 First discovered by McCullough et al. 2 in 1993, GRIM polymerization enables the facile synthesis of conjugated polymers such as poly(3-alkylthiophenes) (P3ATs) with a high degree of regioregularity. 3 In addition, the synthesis of block copolymers and the incorporation of well-defined polymer end groups is permitted.4,5 As a result, P3ATs obtained from GRIM polymerization have been established as hole-transporting organic semiconductors and are among the most applied conjugated polymers. 2,6 For the formation of hybrid optoelectronic devices P3ATs have also been combined with their inorganic analogs, e.g. TiO 2 or CdSe, as this approach enables the utilization of outstanding electron-and hole-transporting materials. While the concept of hybrid solar cells or light-emitting diodes appears to be superior to common organic solar cells, a major task is to enable efficient interaction of polymers and inorganic nanoparticles, avoiding microphase-separation typically occurring for polymer/ nanoparticle blends, as this lowers the overall device performance.6 Consequently and from a chemical aspect, functional end groups facilitating an effective interaction of conjugated polymers with inorganic nanoparticles are desirable for hybrid optoelectronic devices. 7,8 This allows a homogeneous dispersion of inorganic and organic ma...

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Section: Resultsmentioning

confidence: 96%

Section: Materials and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Functionalization of P3HT with Various Mono- and Multidentate Anchor Groups

Menk¹,

Fokina²,

Oschmann³

et al. 2017

J. Braz. Chem. Soc.

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“…Typically, two different synthetic strategies toward polypeptoids are possible: iterative submonomer route and ring‐opening polymerization (ROP) of N ‐substituted α‐amino acid‐ N ‐carboxyanhydrides (NNCAs) . Polypeptoids with absolute monodispersity and controlled sequence can be harvested by submonomer approach.…”

Section: Introductionmentioning

confidence: 99%

Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

2019

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Polypeptoids are peptidomimetic polymers invented in the early 1990s. Although polypeptoid chemistry is developing rapidly, the simple synthesis of polypeptoids and sequence‐controlled polypeptoids still remains a challenge. Fortunately, we have seen a drastic rising trend in the area of Ugi reaction for polypeptoid chemistry. In the following article, recent examples of the Ugi reaction for polypeptoids synthesis will be presented, as will their suitability for sequence‐defined peptide‐peptoid hybrids. The advantages and limitations of the Ugi reaction will be discussed, which is important for the simple and general synthesis of polypeptoids.

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Concepts and Approaches to Reduce or Avoid Protein Corona Formation on Nanoparticles: Challenges and Opportunities

Barz,

Parak,

Zentel

2024

Advanced Science

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This review describes the formation of a protein corona (or its absence) on different classes of nanoparticles, its basic principles, and its consequences for nanomedicine. For this purpose, it describes general concepts to control (guide/minimize) the interaction between artificial nanoparticles and plasma proteins to reduce protein corona formation. Thereafter, methods for the qualitative or quantitative determination of protein corona formation are presented, as well as the properties of nanoparticle surfaces, which are relevant for protein corona prevention (or formation). Thereby especially the role of grafting density of hydrophilic polymers on the surface of the nanoparticle is discussed to prevent the formation of a protein corona. In this context also the potential of detergents (surfactants) for a temporary modification as well as grafting‐to and grafting‐from approaches for a permanent modification of the surface are discussed. The review concludes by highlighting several promising avenues. This includes (i) the use of nanoparticles without protein corona for active targeting, (ii) the use of synthetic nanoparticles without protein corona formation to address the immune system, (iii) the recollection of nanoparticles with a defined protein corona after in vivo application to sample the blood proteome and (iv) further concepts to reduce protein corona formation.

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Multidentate Polysarcosine-Based Ligands for Water-Soluble Quantum Dots

Cited by 49 publications

References 49 publications

Functionalization of P3HT with Various Mono- and Multidentate Anchor Groups

Functionalization of P3HT with Various Mono- and Multidentate Anchor Groups

Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

Concepts and Approaches to Reduce or Avoid Protein Corona Formation on Nanoparticles: Challenges and Opportunities

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