Azido‐Substituted BODIPY Dyes for the Production of Fluorescent Carbon Nanotubes

Fedeli, Stefano; Paoli, Paolo; Brandi, Alberto; Venturini, Lorenzo; Giambastiani, Giuliano; Tuci, Giulia; Cicchi, Stefano

doi:10.1002/chem.201501817

Cited by 18 publications

(21 citation statements)

References 51 publications

(44 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The maximum emission bands were at λ em = 524 nm (λ exc = 380 nm) and λ em = 523 nm (λ exc = 460 nm, see Supporting Information File 1 , Figure S2). Then, a Stokes shift of 16 nm could be appreciated in agreement with data previously reported for PBA-BODIPY ( 1 ) [ 26 , 35 ].…”

Section: Resultssupporting

confidence: 90%

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

Andreozzi

Tamberi

Tasca

et al. 2020

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Mechanochemistry is an emerging and reliable alternative to conventional solution (batch) synthesis of complex molecules under green and solvent-free conditions. In this regard, we report here on the conjugation of a dextran polysaccharide with a fluorescent probe, a phenylboronic acid (PBA)-functionalized boron dipyrromethene (BODIPY) applying the ball milling approach. The ball milling formation of boron esters between PBA BODIPY and dextran proved to be more efficient in terms of reaction time, amount of reactants, and labelling degree compared to the corresponding solution-based synthetic route. PBA-BODIPY dextran assembles into nanoparticles of around 200 nm by hydrophobic interactions. The resulting PBA-BODIPY dextran nanoparticles retain an apolar interior as proved by pyrene fluorescence, suitable for the encapsulation of hydrophobic drugs with high biocompatibility while remaining fluorescent.

show abstract

Section: Resultssupporting

confidence: 90%

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

Andreozzi

Tamberi

Tasca

et al. 2020

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The decoration of the carbonaceous substrates, 4 and 5 , with (4-ethynylphenyl)diphenylphosphine oxide ( 3 ), via the CuAAC reaction, required their previous modification with the introduction of azido groups. For this purpose, CNMs 4 and 5 were reacted with 4-azidoaniline ( 10 ) following, again, the Tour protocol affording compounds 11 and 12 ( Scheme 3 ) [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

Nanostructured carbon materials decorated with organophosphorus moieties: synthesis and application

Biagiotti¹,

Langé²,

Ligi³

et al. 2017

Beilstein J. Nanotechnol.

Self Cite

View full text Add to dashboard Cite

A new synthetic approach for the production of carbon nanomaterials (CNM) decorated with organophosphorus moieties is presented. Three different triphenylphosphine oxide (TPPO) derivatives were used to decorate oxidized multiwalled carbon nanotubes (ox-MWCNTs) and graphene platelets (GPs). The TPPOs chosen bear functional groups able to react with the CNMs by Tour reaction (an amino group), nitrene cycloaddition (an azido group) or CuAAC reaction (one terminal C–C triple bond). All the adducts were characterized by FTIR, Raman spectroscopy, TEM, XPS, elemental analysis and ICP-AES. The cycloaddition of nitrene provided the higher loading on ox-MWCNTs and GPs as well, while the Tour approach gave best results with nanotubes (CNTs). Finally, we investigated the possibility to reduce the TPPO functionalized CNMs to the corresponding phosphine derivatives and applied one of the materials produced as heterogeneous organocatalyst in a Staudinger ligation reaction.

show abstract

“…With acyl chloride instead of aldehyde as the substrate, the synthesis of NB-1 was much cleaner, and the compound could be easily isolated with a 67% overall yield. Then, Knoevenagel condensation was carried out in refluxing acetonitrile with freshly dried molecular sieves, as proposed by Cicchi and coworkers [33]. This method gave NB-2 with a satisfactory yield of 40%.…”

Section: Synthesis and Spectral Chracteristics Of Nb-2mentioning

confidence: 99%

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

et al. 2020

View full text Add to dashboard Cite

Herein, we describe the synthesis of a fluorescent probe NB-2 and its use for the detection of peroxyl radicals. This probe is composed of two receptor segments (4-hydroxycinnamyl moieties) sensitive towards peroxyl radicals that are conjugated with a fluorescent reporter, dipyrrometheneboron difluoride (BODIPY), whose emission changes depend on the oxidation state of the receptors. The measurement of the rate of peroxidation of methyl linoleate in a micellar system in the presence of 1.0 µM NB-2 confirmed its ability to trap lipid peroxyl radicals with the rate constant kinh = 1000 M−1·s−1, which is ten-fold smaller than for pentamethylchromanol (an analog of α-tocopherol). The reaction of NB-2 with peroxyl radicals was further studied via fluorescence measurements in methanol, with α,α′-azobisisobutyronitrile (AIBN) used as a source of radicals generated by photolysis or thermolysis, and in the micellar system at pH 7.4, with 2,2′-azobis(2-amidinopropane) (ABAP) used as a thermal source of the radicals. The reaction of NB-2 receptors with peroxyl radicals manifests itself by the strong increase of a fluorescence with a maximum at 612–616 nm, with a 14-fold enhancement of emission in methanol and a 4-fold enhancement in the micelles, as compared to the unoxidized probe. Our preliminary results indicate that NB-2 behaves as a “switch on” fluorescent probe that is suitable for sensing peroxyl radicals in an organic lipid environment and in bi-phasic dispersed lipid systems.

show abstract

Azido‐Substituted BODIPY Dyes for the Production of Fluorescent Carbon Nanotubes

Cited by 18 publications

References 51 publications

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

Nanostructured carbon materials decorated with organophosphorus moieties: synthesis and application

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

Contact Info

Product

Resources

About