Synthesis of an Azide- and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules

Gulumkar, Vijay; Tähtinen, Ville; Ali, Aliaa A.; Rahkila, Jani; Valle‐Delgado, Juan José; Äärelä, Antti; Österberg, Monika; Virta, Pasi

doi:10.1021/acsomega.1c05955

Cited by 5 publications

(8 citation statements)

References 34 publications

(60 reference statements)

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“…This C 60 building‐block was latter used to be functionalized with twelve ‘super‐triarylamine’ fragments for applications as hole‐transporting and electron blocking layers in PerSCs [38] . More recently, an azide‐ and tetrazine‐functionalized [60]fullerene was prepared as an orthogonally bifunctional C 60 scaffold which could be selectively one‐pot functionalized by two pericyclic click reactions [39] …”

Section: Resultsmentioning

confidence: 99%

“…[38] More recently, an azide-and tetrazine-functionalized [60]fullerene was prepared as an orthogonally bifunctional C 60 scaffold which could be selectively one-pot functionalized by two pericyclic click reactions. [39] Since [60]PCBM molecule still remains widely used as electron acceptor in BHJ devices, [40] we have estimated that the modification of the morphology change should be limited when using an azidofullerene derived from this [60]PCBM system. We then developed an original and powerful approach to synthesize [60]PCBÀ C 3 À N 3 and [60]PCBÀ C 6 À N 3 azidofullerenes to demonstrate increased stability with suppression of macrophase separation after thermal annealing treatment of the device, as a result of the reaction between the azido group with fullerene.…”

Section: Synthesis and Characterization Of Fullerenes C 60 And C 70 B...mentioning

confidence: 99%

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Azido‐Functionalized Fullerenes, Perylenediimide, Perylene, and Tetraphenylethylene as Crosslinkers for Applications in Materials Science

Hudhomme

Villegas

Diacon

et al. 2023

Helvetica Chimica Acta

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This study presents the synthesis and characterization of novel azido molecules with demonstrated crosslinking ability when used as additives in polymer/fullerene organic solar cells. These compounds derived from fullerenes C60 and C70, or dyes from perylenediimide, perylene and tetraphenylethylene frameworks, bearing a different number of azido groups, are of particular interest to stabilize and increase the thermal stability of the device morphology. In particular, the electro and photoactive dye derivatives allow the introduction of additional functionality with the possibility of extending the absorption domain of the photoactive layer. In addition, and more broadly, such azido crosslinkers could find applications in the field of optoelectronic devices as a simple and cheap strategy to improve the performance and long‐term stability of organic solar cells, perovskites solar cells, or organic light‐emitting diodes.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Characterization Of Fullerenes C 60 And C 70 B...mentioning

confidence: 99%

Azido‐Functionalized Fullerenes, Perylenediimide, Perylene, and Tetraphenylethylene as Crosslinkers for Applications in Materials Science

Hudhomme

Villegas

Diacon

et al. 2023

Helvetica Chimica Acta

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“…Additionally, MSNAs can be specifically heterofunctionalized with tissue-specific ligands or labeling groups making them interesting tools for therapeutic and diagnostic applications. 31,32 In this work, we demonstrate site-specific introduction of radiolabel to [60] and 2). The ON sequence selected for this study has been previously used as a model sequence in the assembly of SNAs.…”

Section: ■ Introductionmentioning

confidence: 87%

In Vivo Imaging of [60]Fullerene-Based Molecular Spherical Nucleic Acids by Positron Emission Tomography

et al. 2023

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fullerene-based molecular spherical nucleic acids (MSNAs), consisting of a human epidermal growth factor receptor 2 (HER2) mRNA antisense oligonucleotide sequence with a native phosphodiester and phosphorothioate backbone, were synthesized, site-specifically labeled with a positron emitting fluorine-18 and intravenously administrated via tail vein to HER2 expressing HCC1954 tumor-bearing mice. The biodistribution of the MSNAs was monitored in vivo by positron emission tomography/computed tomography (PET/CT) imaging. MSNA with a native phosphodiester backbone (MSNA-PO) was prone to rapid nuclease-mediated degradation, whereas the corresponding phosphorothioate analogue (MSNA-PS) with improved enzymatic stability showed an interesting biodistribution profile in vivo. One hour after the injection, majority of the radioactivity was observed in spleen and liver but also in blood with an average tumor-tomuscle ratio of 2. The prolonged radioactivity in blood circulation may open possibilities to the targeted delivery of the MSNAs.

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“…In the last part of this work, we focused our attention on the synthesis of heterosubstituted C 60 scaffolds. Actually, a few studies of hetero-functionalization of C 60 are described in literature [44,45], and there are no examples of C 60 functionalization with both sugar and amino acid derivatives through the use of malondiamide-based linkers.…”

Section: Introductionmentioning

confidence: 99%

Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers

et al. 2022

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In the last few years, nanomaterials based on fullerene have begun to be considered promising tools in the development of efficient adjuvant/delivery systems for vaccination, thanks to their several advantages such as biocompatibility, size, and easy preparation and modification. In this work we reported the chemoenzymatic synthesis of natural polymannan analogues (di- and tri-mannan oligosaccharides characterized by α1,6man and/or α1,2man motifs) endowed with an anomeric propargyl group. These sugar derivatives were submitted to 1,3 Huisgen dipolar cycloaddition with a malondiamide-based chain equipped with two azido terminal groups. The obtained sugar-modified malondiamide derivatives were used to functionalize the surface of Buckminster fullerene (C60) in a highly controlled fashion, and yields (11–41%) higher than those so far reported by employing analogue linkers. The same strategy has been exploited to obtain C60 endowed with natural and unnatural amino acid derivatives. Finally, the first double functionalization of fullerene with both sugar- and amino acid-modified malondiamide chains was successfully performed, paving the way to the possible derivatization of fullerenes with immunogenic sugars and more complex antigenic peptides.

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Synthesis of an Azide- and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules

Cited by 5 publications

References 34 publications

Azido‐Functionalized Fullerenes, Perylenediimide, Perylene, and Tetraphenylethylene as Crosslinkers for Applications in Materials Science

Azido‐Functionalized Fullerenes, Perylenediimide, Perylene, and Tetraphenylethylene as Crosslinkers for Applications in Materials Science

In Vivo Imaging of [60]Fullerene-Based Molecular Spherical Nucleic Acids by Positron Emission Tomography

Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers

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