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Self-Assembly Concepts, Properties, and Applications polymers Review Patchy Micelles with a Crystalline Core: Self-Assembly Concepts, Properties, and Applications Christian Hils 1, Ian Manners 2, Judith Schöbel 3,* and Holger Schmalz 1,4,* 1 Macromolecular Chemistry II, University of Bayreuth, Universitätsstraße 30, 95440 Bayreuth, Germany; [email protected] 2 Department of Chemistry, University of Victoria, 3800 Finnerty Road, Victoria, BC V8P 5C2, Canada; [email protected] 3 Fraunhofer Institute for Applied Polymer Research IAP, Geiselbergstraße 69, 14476 Potsdam-Golm, Germany 4 Bavarian Polymer Institute (BPI), University of Bayreuth, Universitätsstraße 30, 95440 Bayreuth, Germany * Correspondence: [email protected] (J.S.); [email protected] (H.S.) Abstract: Crystallization-driven self-assembly (CDSA) of block copolymers bearing one crystallizable block has emerged to be a powerful and highly relevant method for the production of one- and two-dimensional micellar assemblies with controlled length, shape, and corona chemistries. This gives access to a multitude of potential applications, from hierarchical self-assembly to complex superstructures, catalysis, sensing, nanomedicine, nanoelectronics, and surface functionalization. Related to these applications, patchy crystalline-core micelles, with their unique, nanometer-sized, alternating corona segmentation, are highly interesting, as this feature provides striking advantages concerning interfacial activity, functionalization, and confinement effects. Hence, this review aims to provide an overview of the current state of the art with respect to self-assembly concepts, properties, and applications of patchy micelles with crystalline cores formed by CDSA. We have also included a more general discussion on the CDSA process and highlight block-type co-micelles as a special Citation: Hils, C.; Manners, I.; Schöbel, J.; Schmalz, H. Patchy type of patchy micelle, due to similarities of the corona structure if the size of the blocks is well Micelles with a Crystalline Core: below 100 nm. Self-Assembly Concepts, Properties, and Applications. Polymers 2021, 13, Keywords: crystallization-driven self-assembly (CDSA); crystalline-core micelles; patchy micelles; 1481. https://doi.org/10.3390/ block copolymers polym13091481 Academic Editor: Stefano Leporatti 1. Introduction Received: 8 April 2021 The solution self-assembly of block copolymers (BCPs) has paved the way to a vast Accepted: 1 May 2021 number of micellar assemblies of various shapes (e.g. spheres, cylinders, vesicles, platelets, Published: 4 May 2021 core-shell, core-shell-corona, and compartmentalized (core or corona) structures) and hierarchical superstructures, as well as hybrids with fascinating applications in drug Publisher’s Note: MDPI stays neutral delivery and release, as emulsifiers/blend compatibilizers, in nanoelectronics, as responsive with regard to jurisdictional claims in materials (temperature, pH, light), templates for nanoparticles, in heterogeneous catalysis, published maps and institutional affil- etc. [1–6]. A key prerequisite for controlling/programming the solution self-assembly is iations. the synthesis of well-defined diblock and triblock (linear, star-shaped, ABA- or ABC-type) copolymers via controlled or living polymerization techniques, such as living anionic polymerization, reversible addition−fragmentation chain transfer, nitroxide-mediated, and atom transfer radical polymerization [5–9]. In general, anisotropic polymer micelles Copyright: © 2021 by the authors. can be divided into three main categories: multicompartment core micelles (MCMs), Licensee MDPI, Basel, Switzerland. surface-compartmentalized micelles, and a combination of both [2]. MCMs are generally This article is an open access article defined as micellar assemblies with a solvophilic corona and a microphase-separated distributed under the terms and solvophobic core. According to the suggestion of Laschewsky et al., a key feature of conditions of the Creative Commons Attribution (CC BY) license (https:// multicompartment micelles is that the various sub-domains in the micellar core feature creativecommons.org/licenses/by/ substantially different properties to behave as separate compartments [10,11]. MCMs 4.0/). are commonly prepared via hierarchical self-assembly of suitable building blocks, which Polymers 2021, 13, 1481. https://doi.org/10.3390/polym13091481 https://www.mdpi.com/journal/polymers Polymers 2021, 13, x FOR PEER REVIEW 2 of 25 compartment micelles is that the various sub-domains in the micellar core feature sub- stantially different properties to behave as separate compartments [10,11]. MCMs are commonly prepared via hierarchical self-assembly of suitable building blocks, which pro- vide “sticky patches” [12–15]. Depending on the number and geometrical arrangement Polymers(linear,2021 ,triangular,13, 1481 tetrahedral, etc.) of the “sticky patches”, as well as the volume fraction2 of 26 of the solvophilic block, various spherical, cylindrical, sheet-like, and vesicular MCMs are accessible [16–25]. For a deeper insight into this highly relevant topic, the reader is re- provide “sticky patches” [12–15]. Depending on the number and geometrical arrangement ferred to recent extensive(linear, reviews triangular, on tetrahedral, MCMs [26 etc.)–31]. of the Surface “sticky- patches”,compartmentalized as well as the volume micelles fraction are subdivided into micellesof the solvophilic with a block,Janus various-type spherical,(two opposing cylindrical, faces sheet-like, with and different vesicular chem- MCMs are istry or polarity) or patchaccessible-like, [16 microphase–25]. For a deeper-separated insight into corona, this highly featuring relevant topic, several the reader compart- is referred ments of different chemistryto recent or extensive polarity reviews (denoted on MCMs as patchy [26–31]. micelles), Surface-compartmentalized as illustrated micellesin Fig- are subdivided into micelles with a Janus-type (two opposing faces with different chemistry ure 1 for cylindrical micelles.or polarity) Here, or patch-like, block microphase-separated co-micelles with corona,a block featuring-like arrangement several compartments of several (>2) surface compartmentsof different chemistry along or polaritythe cylindrical (denoted as long patchy axis micelles), can be as illustratedregarded in Figureas a 1 special case of patchy formicelles. cylindrical It is micelles. noted Here, that block AB- co-micellestype diblock with co a block-like-micelles arrangement also represent of several (>2) surface compartments along the cylindrical long axis can be regarded as a special Janus-type micelles, wherecase of the patchy two micelles. opposing It is noted faces that are AB-type arranged diblock perpendicular co-micelles alsorepresent to the cy- Janus- lindrical long axis. Thetype broken micelles, symmetry where the twoof Janus opposing particles faces are arrangedoffers efficient perpendicular and todistinctive the cylindrical means of targeting complexlong axis. materials The broken symmetryby hierarchical of Janus particles self-assem offers efficientbly and and realize distinctive unique means of targeting complex materials by hierarchical self-assembly and realize unique properties and properties and applications,applications, like like particulate particulate surfactants,surfactants, optical optical nanoprobes, nanoprobes, biosensors, biosensors, self-propulsion, self-propulsion, and manyand many more more [32 [32–41].–41]. Figure 1.Figure Schematic 1. Schematic depiction depiction of of aa cylindricalcylindrical (a) Janus (a) Janus micelle, micelle, (b) block co-micelle,(b) block and co- (cmicelle,) patchy micelle. and (c) patchy micelle. For the preparation of patchy micelles and polymersomes from amorphous BCPs, three main strategies can be applied: (i) self-assembly of ABC triblock terpolymers in selective For the preparationsolvents of patchy for the incompatible micelles Aand and Cpolymersomes blocks [42–48]; (ii) co-assemblyfrom amorphous of AB and CDBCPs, diblock three main strategies cancopolymers be applied: with selective (i) self interactions-assembly between of ABC the B triblock and C blocks terpolymers (e.g. hydrogen in bonding, se- ionic interactions, solvophobic interactions) [49–52], resulting in patchy micelles with an lective solvents for theinsoluble incompatible mixed B/C A core; and and C (iii)blocks co-assembly [42–48]; of AB (ii) and co BC-assembly diblock copolymers of AB and [53–56 ] CD diblock copolymerswhere with the selective B block forms interactions the insoluble between core. However, the B mostly and sphericalC blocks micelles (e.g. orhy- poly- drogen bonding, ionicmersomes interactions, with a solvophobic patchy corona have interactions) been reported [49 and–52], only resulting a few reports in describepatchy the preparation of one-dimensional (worm-like, cylindrical) assemblies with a patch-like com- micelles with an insolublepartmentalized mixed corona,B/C core; even and though (iii) theoretical co-assembly work on of mixed AB polymer and BC brushes diblock predict copolymers [53–56] wheretheir existence the B block [57–61 ].forms One of the rare insoluble but highly core. intriguing However, examples mostly are PtBA– spheri-b–PCEMA– cal micelles or polymersomesb–PGMA (poly( withtert a-butyl patchy acrylate)– coronablock have–poly(2-cinnamoyloxyethyl been reported and methacrylate)– only a fewblock – poly(glyceryl monomethacrylate)) and PnBA–b–PCEMA–b–PtBA (PnBA: poly(n-butyl reports describe the preparationacrylate))
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