Adamantane Research Articles

Adamantyl and carbazole containing trans-poly(norbornene-dicarboximide)s as electro-optic chromophore hosts

A selection of trans-poly(norbornene-dicarboximide) random copolymers incorporating adamantyl and carbazole groups have been prepared using the Grubbs 1st generation catalyst. The copolymer with the greatest carbazole content was employed as a host for a high activity chromophore guest. The adamantyl groups were able to elevate the glass transition and thermal decomposition temperatures of the host copolymers, while the carbazole groups were included to facilitate the dispersion of the added chromophores and enhance the poling process. The mass of the adamantyl pendant monomer was kept constant as the mass of the carbazole pendant monomer was increased gradually. The successful incorporation of the carbazole moiety into the copolymers was confirmed by 1H NMR integration. The polymers had a predominantly trans microstructure and the cis/trans ratio did not change significantly. The polymer molecular weights increased linearly from 25,758 g/mol to 56,827 g/mol as more carbazole-pendant monomer was incorporated. Polydispersities ranged from 1.29 to 1.70 and elemental analysis confirmed an ascending carbon% in the polymers from 72.29% to 76.26%. The glass transition temperatures decreased from 240 °C to 126 °C, with the thermal decomposition temperatures (10% loss) remaining relatively constant at between 423 °C to 394 °C, indicating the polymers had a good thermal stability. The chromophore guest concentration was increased gradually into the copolymer host from 15 wt% to 65 wt%. When poled at a field of 50 V/μm in thin film it was found that the optimum poling temperature decreased linearly from 150 °C to 90 °C as the chromophore concentration was increased, a maximum poling efficiency of 1.02 was achieved at a chromophore concentration of 55 wt%.

Adamantane-Modified Graphene Oxide for Cyanate Ester Resin Composites with Improved Properties

The conjugation of graphene and polymers has attracted great attention for the fabrication of functional hybrid nanomaterials. Here, we demonstrate the modification of graphene oxide (GO) with adamantane (AMT) through the diimide-activated amidation reaction. The modification of GO with AMT improves the dispersion and decreases the interfacial polarization of GO, causing a lower dielectric constant for the fabricated GO/AMT hybrid materials. The structures of GO/AMT were studied by Fourier transform infrared spectroscopy and Raman spectroscopy. Furthermore, the mechanical properties, thermal stability, and dielectric constant of GO/AMT composites were measured at a low cured temperature using various techniques, such as differential scanning calorimetry, thermogravimetric analysis, and dynamic mechanical thermal analysis. It was found that the synthesized GO/AMT materials with different contents were blended into cyanate ester (CE) resins, resulting in a lower cure temperature, smaller dielectric constant, higher thermal stability, and stronger water resistance. It is expected that this novel GO/AMT-CE material will have potential applications for replacing traditional thermosetting resins.

Experimental Characterization of Droplet Adhesion: The Ejection Test Method (ETM) Applied to Surfaces with Various Hydrophobicity

We study the wetting and the adhesive behavior of substrates made by electropolymerization of copolymers of pyrene substituted with fluoroalkyl and adamantyl groups. The hydrophobicity and water adhesion properties can be tuned by the molar percentage (mol %) of each pyrene monomer so that the substrate properties can vary from superhydrophobic to parahydrophobic, with respectively low and high water adhesion. The ejection test method (ETM) is proposed as an original tool to discriminate and characterize such substrates. Using a catapult-like apparatus, a droplet initially at rest on the surface is subject to a large acceleration and is subsequently ejected. Depending on the surface properties and initial catapult acceleration, the ejection is more or less efficient and occurs with or without fragmentation of the droplet. The ETM is shown to be a complementary test to the lateral adhesion and hysteresis classical measurements. This work is of importance for the understanding of adhesion phenomena on various surfaces and for a better quantitative characterization of their adhesive properties.

Optimization and Lead Selection of Benzothiazole Amide Analogs Toward a Novel Antimycobacterial Agent.

Mycobacteria remain an important problem worldwide, especially drug resistant human pathogens. Novel therapeutics are urgently needed to tackle both drug-resistant tuberculosis (TB) and difficult-to-treat infections with nontuberculous mycobacteria (NTM). Benzothiazole adamantyl amide had previously emerged as a high throughput screening hit against M. tuberculosis (Mtb) and was subsequently found to be active against NTM as well. For lead optimization, we applied an iterative process of design, synthesis and screening of several 100 analogs to improve antibacterial potency as well as physicochemical and pharmacological properties to ultimately achieve efficacy. Replacement of the adamantyl group with cyclohexyl derivatives, including bicyclic moieties, resulted in advanced lead compounds that showed excellent potency and a mycobacteria-specific spectrum of activity. MIC values ranged from 0.03 to 0.12 μg/mL against M. abscessus (Mabs) and other rapid- growing NTM, 1–2 μg/mL against M. avium complex (MAC), and 0.12–0.5 μg/mL against Mtb. No pre-existing resistance was found in a collection of n = 54 clinical isolates of rapid-growing NTM. Unlike many antibacterial agents commonly used to treat mycobacterial infections, benzothiazole amides demonstrated bactericidal effects against both Mtb and Mabs. Metabolic labeling provided evidence that the compounds affect the transfer of mycolic acids to their cell envelope acceptors in mycobacteria. Mapping of resistance mutations pointed to the trehalose monomycolate transporter (MmpL3) as the most likely target. In vivo efficacy and tolerability of a benzothiazole amide was demonstrated in a mouse model of chronic NTM lung infection with Mabs. Once daily dosing over 4 weeks by intrapulmonary microspray administration as 5% corn oil/saline emulsion achieved statistically significant CFU reductions compared to vehicle control and non-inferiority compared to azithromycin. The benzothiazole amides hold promise for development of a novel therapeutic agent with broad antimycobacterial activity, though further work is needed to develop drug formulations for direct intrapulmonary delivery via aerosol.

Versatile Redox-Responsive Polyplexes for the Delivery of Plasmid DNA, Messenger RNA, and CRISPR-Cas9 Genome-Editing Machinery.

Gene therapy holds great promise for the treatment of many diseases, but clinical translation of gene therapies has been slowed down by the lack of safe and efficient gene delivery systems. Here, we report two versatile redox-responsive polyplexes (i.e., cross-linked and non-crosslinked) capable of efficiently delivering a variety of negatively charged payloads including plasmid DNA (DNA), messenger RNA, Cas9/sgRNA ribonucleoprotein (RNP), and RNP-donor DNA complexes (S1mplex) without any detectable cytotoxicity. The key component of both types of polyplexes is a cationic poly( N, N'-bis(acryloyl)cystamine- co-triethylenetetramine) polymer [a type of poly( N, N'-bis(acryloyl)cystamine-poly(aminoalkyl)) (PBAP) polymer] containing disulfide bonds in the backbone and bearing imidazole groups. This composition enables efficient encapsulation, cellular uptake, controlled endo/lysosomal escape, and cytosolic unpacking of negatively charged payloads. To further enhance the stability of non-crosslinked PBAP polyplexes, adamantane (AD) and β-cyclodextrin (β-CD) were conjugated to the PBAP-based polymers. The cross-linked PBAP polyplexes formed by host-guest interaction between β-CD and AD were more stable than non-crosslinked PBAP polyplexes in the presence of polyanionic polymers such as serum albumin, suggesting enhanced stability in physiological conditions. Both cross-linked and non-crosslinked polyplexes demonstrated either similar or better transfection and genome-editing efficiencies, and significantly better biocompatibility than Lipofectamine 2000, a commercially available state-of-the-art transfection agent that exhibits cytotoxicity.

Inhibitors of the M2 Proton Channel Engage and Disrupt Transmembrane Networks of Hydrogen-Bonded Waters

Water-mediated interactions play key roles in drug binding. In protein sites with sparse polar functionality, a small-molecule approach is often viewed as insufficient to achieve high affinity and specificity. Here we show that small molecules can enable potent inhibition by targeting key waters. The M2 proton channel of influenza A is the target of the antiviral drugs amantadine and rimantadine. Structural studies of drug binding to the channel using X-ray crystallography have been limited because of the challenging nature of the target, with the one previously solved crystal structure limited to 3.5 Å resolution. Here we describe crystal structures of amantadine bound to M2 in the Inwardclosed conformation (2.00 Å), rimantadine bound to M2 in both the Inwardclosed (2.00 Å) and Inwardopen (2.25 Å) conformations, and a spiro-adamantyl amine inhibitor bound to M2 in the Inwardclosed conformation (2.63 Å). These X-ray crystal structures of the M2 proton channel with bound inhibitors reveal that ammonium groups bind to water-lined sites that are hypothesized to stabilize transient hydronium ions formed in the proton-conduction mechanism. Furthermore, the ammonium and adamantyl groups of the adamantyl-amine class of drugs are free to rotate in the channel, minimizing the entropic cost of binding. These drug-bound complexes provide the first high-resolution structures of drugs that interact with and disrupt networks of hydrogen-bonded waters that are widely utilized throughout nature to facilitate proton diffusion within proteins.

Discovery of benzothiazole amides as potent antimycobacterial agents

From a high throughput screening of commercially available libraries against nontuberculous mycobacteria and Mycobacterium tuberculosis, numerous hits were identified with moderate activity. Extensive medicinal chemistry optimization has led to a series of potent benzothiazole amide antimycobacterial agents. Replacement of the adamantyl group with cyclohexyl derivatives and further development of this series resulted in an advanced lead compound, CRS400393, which demonstrated excellent potency and a mycobacteria-specific spectrum of activity. MIC values ranged from 0.03 to 0.12 μg/mL against Mycobacterium abscessus and other rapid-grower NTM, and 1–2 μg/mL against Mycobacterium avium complex. The preliminary mechanism of action studies suggested these agents may target MmpL3, a mycobacterial mycolic acid transporter. The series has demonstrated in vivo efficacy in a proof of concept mouse model of M. abscessus infection.

Synthesis and biological activity of novel adamantan-based dialkylaminopropanol quaternary salts

The emergence and spread of multidrug-resistant pathogens leads to a decrease in efficacy of antibiotic therapy, prolongation of the length of patient’s hospital stay and an increase in treatment costs. The screening of potential antimicrobial agents among the new classes of chemical compounds is one of the promising methods to overcome the problem of resistance.Objectives. The synthesis and screening studies of antimicrobial activity of quaternary salts of adamantane derivatives (3a – 3l) with the aim to find of new prospective compound with good activityMaterials and methods. The synthesis and investigation of physicochemical properties of new adamantan-based dialkylaminopropanol quaternary salts were carried out. The evaluation of antimicrobial action against S. aureus, E. coli and C. albicans strains were performed.Results and discussion. The results showed that the inhibitory activities of quaternary salts with 1-adamantylethyl radical in their alkoxy group were significantly higher than those of the compounds with 1-adamantyl and 1-adamantyloxyethyl radicals in their alkoxy group.Conclusions. 3c was the most active compound tested against all strains, with MIC between 1.56 and 3.12 µg/mL, and its antimicrobial activity was similar to that of myramistin.

Antibiofilm activity of aminopropanol derivatives against Pseudomonas aeruginosa

Bacterial biofilm, particularly formed by Pseudomonas aeruginosa, are a cause of severe chronic infectious diseases. Bacteria within a biofilm are phenotypically more resistant to antibiotics and the macroorganism immune system, making it an important virulence factor for many microbes.
 The aminopropanol derivatives with adamantyl (KVM-97) and N-alkylaryl radicals (KVM-194, KVM-204, KVM-261, and KVM-262) were used as study object. The aim of this study was to investigate the antibiofilm activity of compounds on biofilm formation and on mature biofilm of P. aeruginosa. The effects of the aminopropanol derivatives on the biofilm mass were evaluated by using crystal violet assay. Ciprofloxacin, meropenem, ceftazidime, gentamicin were used as reference substances.
 Reported results demonstrate that all compounds displayed antibiofilm activity at the tested concentrations. Remarkable reduction in biofilm formation of P. aeruginosa was found after treatment with KVM-97, KVM-261 and KVM-262 in high concentration (5× MIC), biofilm inhibition activity were 84.3%, 90.5% and 83.3% respectively.
 After a treatment with KVM-204 at 250 μg/ml (5× MIC) 76.6% of the preformed 24-hr biofilms were destroyed. Furthermore, compounds KVM-97, KVM-194, and KVM-261 in both concentrations showed potent antibiofilm activity against the P. aeruginosa, inhibition activity values being between 56.7 and 65.7%.
 All tested compounds in dose-dependent manner exhibited pronounced inhibition activity against mature 5-days P. аeruginosa biofilm.
 It was also observed that tested compounds show high antibiofilm activity in comparison to reference antimicrobials.
 The aminopropanol derivatives may provide templates for a new group of antimicrobial agents and potential future therapeutics for treating chronic infections.

Effect of N-Alkyl Substituents on the Hierarchical Self-Assembly of β-Cyclodextrin-Linked Pyrene-Pyromellitic Diimide Charge-Transfer Complexes.

Hierarchical self-assemblies of β-cyclodextrin-linked pyrene and N-alkyl derivatives of pyromellitic diimides are studied in detail. The charge-transfer interaction between pyrene and pyromellitic diimide is augmented by β-cyclodextrin-pyromellitic diimide binding interactions in these cases. When the alkyl group is adamantyl, a 1:1 complex was formed with a very high association constant (Ka =1.82×106 m-1 ). Here, the charge-transfer interaction is reinforced by inclusion binding of the adamantyl group in the β-cyclodextrin cavity leading to the formation of 2D sheets, which undergo twisting to give twisted fibres. When the alkyl group is tert-butyl, a 1:2 complex was formed with a high association constant (Ka =2.91×104 m-1 ). A detailed analysis showed that the tert-butyl pyromellitic diimide undergoes both inclusion and rim-binding interactions with the β-cyclodextrin. The charge-transfer complex further self-assembled into chiral nanostructures as evident from SEM, TEM and AFM analysis. In the case of N-methyl-substituted pyromellitic diimide, the interaction with β-cyclodextrin-linked pyrene was only through rim binding, which resulted in the formation of a weak charge-transfer complex with Ka =4.2×103 m-1 . Formation of a hierarchical assembly was not observed in this case. A rational mechanism for the self-assembly, which relies on the strength of the cyclodextrin-pyromellitic diimide complexation is presented.

Synthesis of polymers carrying adamantyl substituents in side chain

This review addresses the synthesis of various polymers carrying bulky and rigid adamantyl substituents in their side chains. Synthetic methods for these polymers include typical polymer reactions of introducing adamantyl groups into existing polymers and the polymerization of monomers bearing pendant adamantyl groups. In particular, with regard to the latter synthetic method, the addition polymerization of adamantyl-containing vinyl monomers such as α-olefins, acetylenes, (meth)acrylates, (meth)acrylamides, vinyl ethers, 1,3-dienes, and styrenes is described. A variety of vinyl monomers are capable of undergoing living anionic polymerization to afford polymers with predictable molecular weights and narrow molecular weight distributions (M w/M n = 1.1). In several cases, the introduced adamantyl groups afford steric hindrance to prevent side reactions and control the addition modes of the polymerization. In general, the resulting adamantyl-substituted polymers show extremely high glass transition temperatures and high thermal stability derived from the stiff adamantyl substituents compared with the corresponding parent polymers. This review deals with the synthesis of various polymers carrying bulky and rigid adamantyl substituents in the side chain. The synthetic methods of those polymers include the typical polymer reaction by introducing adamantyl groups to the present polymers and the polymerization of the monomers bearing the adamantyl pendant groups. A variety of vinyl monomers, such as styrenes, 1,3-butadiene, and (meth)acrylates, are capable of the living anionic polymerization to afford the polymers having predictable molecular weights and narrow molecular weight distributions (Mw/Mn =1.1). The resulting adamantyl-substituted polymers show extremely high glass transition temperatures and high thermal stability derived from the stiff adamantyl substituents compared with the corresponding parent polymers.

High refractive index adamantane‐based silicone resins for the encapsulation of light‐emitting diodes

The encapsulation of high power light emitting diode (LED) needs the silicone resins to have relative high refractive index and thermal‐aging properties. Herein, high refractive index adamantane‐based phenyl epoxy‐silicone (APES) resins for LED encapsulation were synthesized by the sol‐gel condensation of 1‐adamantane methanol propyltrimethoxysilane‐3‐urethane, γ‐(2,3‐epoxypropoxy)propytrimethoxysilane and diphenylsilanediol. These adamantane‐based silicone resins have multifunctional groups including adamantyl group, phenyl group, and epoxy group in order to meet the various requirements for LED encapsulation. Importantly, the adamantane group in the silicone resins benefits for high refractive index and anti‐thermal properties. These APES resins were characterized by proton nuclear magnetic resonance and Fourier transform infrared spectroscopy. When APES resins were cured by methylhexahydrophthalic anhydride, they showed relatively high refractive index of 1.56, high hardness, and high thermal resistance. The encapsulated LED demonstrated high adhesion properties by red‐ink tests. These merits make adamantane‐based silicone resins promising candidates as LED encapsulation materials.

Adamantanes Enhance the Photovoltaic Performance and Operational Stability of Perovskite Solar Cells by Effective Mitigation of Interfacial Defect States

AbstractPassivation of electronic defects is an effective strategy to boost the performance and operational stability of perovskite solar cells (PSCs). Identifying molecular materials that achieve this purpose is a key target of current research efforts. Here, adamantane (AD) and 1‐adamantylamine (ADA) are introduced as molecular modulators to abate electronic defects present within the bulk and at the perovskite–hole conductor interface. To this effect, the modulator is added either into the antisolvent (AS) to precipitate it together with the perovskite (AS method) or they are spin coated (SC) onto its surface (SC method). Time‐resolved photoluminescence measurements show substantially longer lifetimes for perovskite films treated with AD and ADA compared to the reference sample. In line with this observation, it is found that the presence of AD and ADA molecules at the interface between the perovskite film and the hole conductor increases all photovoltaic metrics, in particular the open circuit photovoltage (V oc) as well as the operational stability of the PSC.

Solubilization ability of N,N-dimethyl-N-alkyladamantylammonium bromide

Adamantane is difficult to dissolve in water owing to its bulky steric hydrocarbon structure. We designed a novel amphiphilic molecule by introducing an alkyl chain and a cation group into an adamantyl group. N,N-dimethyl-N-alkyladamantylammonium bromide (CnAdAB; n is the alkyl chain length, where n=10, 12, and 14) dissolves easily in water by forming micelles above the critical micelle concentration. Aggregates of this surfactant series form small nonspherical micelles several nanometers in size with relative small aggregation number; 53 (n=10), 59 (n=12), and 63 (n=14) at the typical concentration. Small-angle X-ray scattering measurement showed that the micellar structure of C12AdAB was changed slightly by solubilization of naphthalene and stearic acid. Moreover, the solubilization ability of the aggregates was studied using naphthalene and long-alkyl-chain fatty acids (myristic, palmitic, and stearic acids). The same solubilization experiments were performed using typical cationic surfactants (dodecyltrimethylammonium bromide and a gemini surfactant) for comparison. The molar solubilization ratios indicate that the CnAdAB series can solubilize the aromatic compound naphthalene as well as the other surfactants, whereas they can barely solubilize the long-alkyl-chain fatty acids. The solubilization stability can be analyzed by estimating the Gibbs free energy change (ΔG0) for the transfer of solubilizate molecules to the aggregate phase. The gemini surfactant system showed the largest negative value of ΔG0 for both naphthalene and the fatty acids. On the other hand, solubilization of fatty acids into CnAdAB micelles was not advantageous energetically. These results indicate that the solubilization ability of CnAdAB surfactants is not generally suitable for solubilization of long-alkyl-chain fatty acids owing to the smallness of the micelles.

Temperature and Recognition Dual Responsive Poly(N-Isopropylacrylamide) and Poly(N,N-Dimethylacrylamide) with Adamantyl Side Group.

A series of copolymers with an adamantyl side group (poly(NIPAM-co-AdMA) and poly(DMAM-co-AdMA)) were prepared by radical copolymerization of N-isopropylacrylamide (NIPAM) and N,N-dimethylacrylamide (DMAM) with a 2-methyl-2-adamantylmethacrylate (AdMA) monomer. The structure and composition of the as-synthesized copolymers were characterized by Fourier transform infrared (FT-IR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy, gel permeation chromatography (GPC), thermogravimetric analysis (TGA), and elemental analysis. Temperature and recognition dual responsivity of the copolymers was investigated by cloud point (Tcp) and dynamic light scattering (DLS), respectively. The results show that the as-synthesized copolymers are a kind of temperature-responsive polymer with a lower critical solution temperature (LCST). Tcp was approximately consistent with the critical temperature of intermolecular copolymer association (Tass) from DLS. For these copolymers, Tcp decreases with increasing content of AdMA unit in the copolymers. After the addition of β-cyclodextrins (β-CD), Tcp increases, and the increment of Tcp values gradually became large with increasing content of AdMA in the copolymers. It is host-guest molecular recognition of β-CD and adamantyl groups that endows the as-synthesized copolymers with recognition-tunable thermosensitivity.

Thermally Rearranged Polybenzoxazoles Containing Bulky Adamantyl Groups from Ortho-Substituted Precursor Copolyimides

A new nucleophilic monomer (2,2-bis(3-amino-4-hydroxyphenyl)adamantane, ADHAB) having bulky adamantane groups has been synthesized following an efficient synthetic methodology. The main target of this work was to employ a high thermal stable bulky cycloaliphatic moiety as adamantane to obtain aromatic ortho-hydroxypolyimides (poly(o-hydroxyimide)s) able to thermally rearrange to give polybenzoxazole (TR-PBO) materials that could be tested as gas separation membranes. Thus, an array of ortho-acetylcopolyimides, o-acetyl PIs) were prepared by reaction of ADHAB and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (APAF) with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) via chemical imidization. Copolyimides and homopolyimides showed inherent viscosities ranging from 0.49 to 0.70 dL/g and provided good-quality dense membranes. Glass transition temperatures of these o-acetyl copolyimides were higher as the amount of ADHAB increased. The thermal stability of the adamantane moiety during the...

PdII Complexes with N‐(Diadamantylphosphanyl)diaminocarbene and Related Ligands: Synthesis and Catalytic Applications in Intermolecular Alkyne Hydroaminations

A new N‐diadamantylphosphanyldiaminocarbene 5 is prepared, isolated, and characterized. The carbene appears to be much more stable than previously reported di‐tert‐butyl congeners. The molecular structure of the carbene is determined by X‐ray diffraction analysis. A new (diisopropylamino)(diadamantylphosphanyl)carbene 8 is also prepared in situ, but not isolated, since in this case, the adamantyl groups do not render the carbene more stable, with respect to previously known carbenes with di‐tert‐butyl substitution. Carbene 8 reacts in situ with phenylazide to give iminophosphane 9, which is also accessible from carbene 5 upon rearrangement under heating. Stable chelate PdII complexes are synthesized using both carbene 5 and iminophosphane 9 as ligands. The complex with ligand 9 displays very promising catalytic performance in the intermolecular hydroamination of alkynes with primary arylamines.

Shape memory materials based on adamantane-containing polyurethanes.

In this contribution, a series of adamantane (AD)-containing polyurethanes were prepared from 1,3-adamantanediol, 1,4-butanediol and hexamethylene diisocyanate, and the influences of AD on the shape memory behavior of polyurethanes were systematically studied. Due to large steric hindrance, AD was able to disrupt the regular arrangement of polyurethane chains and contributed to forming an amorphous domain. It was found that moderate AD-containing polyurethanes had good mechanical properties and broad glass transition, and shape memory tests confirmed these polyurethanes possessed a shape fixation rate of 98% and shape recovery rate of 91% during a dual-shape memory procedure. Furthermore, they also exhibited a triple-shape memory effect. This work demonstrated a facile and feasible way to prepare polyurethane-based shape memory materials by using adamantane as a functional unit.

Orthogonal supramolecular protein assembly on patterned bifunctional surfaces.

We report successful and selective dual protein assembly on patterned bifunctional βCD-Ni(ii)NTA surfaces, using red fluorescent protein variants with hexahistidine-tags and teal fluorescent protein variants conjugated with a peptide containing three adamantyl groups. We show that dual protein patterns can only be assembled, when opposing supramolecular interactions have been optimized and nonspecific interactions have been sufficiently suppressed.

Phosphorescent cationic iridium(iii) complexes dynamically bound to cyclodextrin vesicles: applications in live cell imaging.

We report cationic Ir(iii) complexes functionalized with adamantyl groups designed to bind to β-cyclodextrin vesicles (CDV) with high affinity (K a = 1 × 106 M-1). The emission of the complexes is tuned by changing the nature of the cyclometalating ligands. The host-guest adduct of CDV and Ir(iii) complexes shows increased and significantly blue-shifted emission due to the lower mobility of the Ir(iii)-complexes residing in the less polar environment of the vesicle surface. Ir(iii)-decorated CDV are efficiently taken up by cells and can be used in live cell imaging. The CDV act as carriers to transport the phosphorescent complexes into cells where they selectively stain mitochondria.