ABSTRACT
To fill the need for environmentally sensitive fluorescent unnatural amino acids able to operate in the red region of the spectrum, we have designed and synthesized Alared, a red solvatochromic and fluorogenic amino acid derived from the Nile Red chromophore. The new unnatural amino acid can be easily integrated into bioactive peptides using classical solid-phase peptide synthesis. The fluorescence quantum yield and the emission maximum of Alared-labeled peptides vary in a broad range depending on the peptide's environment, making Alared a powerful reporter of biomolecular interactions. Due to its red-shifted absorption and emission spectra, Alared-labeled peptides could be followed in living cells with minimal interference from cellular autofluorescence. Using ratiometric fluorescence microscopy, we were able to track the fate of the Alared-labeled peptide agonists of the apelin G protein-coupled receptor upon receptor activation and internalization. Due to its color-shifting environmentally sensitive emission, Alared allowed for distinguishing the fractions of peptides that are specifically bound to the receptor or unspecifically bound to different cellular membranes.
Subject(s)
Amino Acids , Fluorescent Dyes , Microscopy, Fluorescence , Peptides , Fluorescent Dyes/chemistry , Peptides/chemistry , Amino Acids/chemistry , Humans , Microscopy, Fluorescence/methods , Oxazines/chemistry , Solid-Phase Synthesis Techniques , Spectrometry, FluorescenceABSTRACT
Boron dipyrromethene (BODIPY) and its derivatives are known to be efficient photon-harvesting chromophores. However, their study as active materials in bulk heterojunction (BHJ) solar cells is still scarce. In this study, the development of new synthetic ways to design original BODIPY-based dumbbell-shape molecules, including a first 2,3,5,6-tetravinyl aromatic BODIPY molecule, is reported. High fill factors can be obtained in BHJ solar cells when blended with a fullerene derivative, leading to a new record BODIPY-based power conversion efficiency of 5.8 %.
Subject(s)
Boron/chemistry , Electric Power Supplies , Indoles/chemistry , Porphobilinogen/analogs & derivatives , Solar Energy , Chemical Engineering/methods , Fluorescent Dyes , Fullerenes/chemistry , Molecular Conformation , Porphobilinogen/chemistryABSTRACT
The synthesis and photophysical properties of the first examples of iminosugar clusters based on a BODIPY or a pyrene core are reported. The tri- and tetravalent systems designed as molecular probes and synthesized by way of Cu(I)-catalysed azide-alkyne cycloadditions are fluorescent analogues of potent pharmacological chaperones/correctors recently reported in the field of Gaucher disease and cystic fibrosis, two rare genetic diseases caused by protein misfolding.
ABSTRACT
BOPHY dyes bearing bromo (in 5,5'-position) and iodo (in 4,4'-position) were synthesized. Double Knoevenagel reactions allow the extension of conjugation, resulting in an absorption above 625 nm. Selective cross-coupling reactions promoted by palladium(0) and microwave irradiation allow linking of a perylene module. These dyes are highly fluorescent, and the intramolecular cascade energy transfer from the perylene moiety to the BOPHY framework is almost quantitative, providing large virtual Stoke shifts (>5100 cm(-1)).
Subject(s)
Aza Compounds/chemical synthesis , Boron Compounds/chemical synthesis , Fluorescent Dyes/chemical synthesis , Perylene/chemistry , Aza Compounds/chemistry , Boron Compounds/chemistry , Fluorescent Dyes/chemistry , Molecular Structure , Palladium/chemistry , Spectrometry, FluorescenceABSTRACT
Green-absorbing dipyrromethene dyes engineered from bis-vinyl-thienyl modules are planar molecules, exhibiting strong absorption in the 713-724 nm range and displaying comparable electron and hole mobilities in thin films (maximum value 1 × 10(-3) cm(2)/(V·s)). Bulk heterojunction solar cells assembled with these dyes and a fullerene derivative (PC(61)BM) at a low ratio give a power conversion efficiency as high as 4.7%, with short-circuit current values of 14.2 mA/cm(2), open-circuit voltage of 0.7 V, and a broad external quantum efficiency ranging from 350 to 920 nm with a maximum value of 60%.
