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1.
Chem Soc Rev ; 42(3): 1007-50, 2013 Feb 07.
Artículo en Inglés | MEDLINE | ID: mdl-23151610

RESUMEN

Carbohelicenes generally incorporate a helical, distorted, conjugated, polyaromatic system with ortho-fused benzenoid rings, which is a fundamental molecular characteristic of this class of compounds. They have been described as "molecules in distress" due to their distortion. The generation of a chiral helicity in helicenes was observed because of a severe intramolecular steric strain. Helicity is a molecular necessity in the higher series of carbohelicenes, when at some point, a helical pitch occurs when a second coil is formed. The most interesting properties resulting from such molecular distortion are the very high chiroptical and circular dichroism values. For instance, the resolution of some helicene racemates by "hand picking" of a few homochiral single enantiomeric crystals allowed for a measurement of their optical rotation. Due to that intrinsic chirality spanned over a large polyaromatic template, preliminary results clearly established the efficiency of carbohelicenes to induce asymmetry and chirality in organic synthesis and in supramolecular chemistry. Additionally, they have some potential uses in several fields: materials science, nanoscience, chemical biology and supramolecular chemistry. It has encouraged many attempts to develop new asymmetric syntheses of carbohelicenes, as well as some chiral separations of enantiomers and diastereoisomers. This review is thus dedicated to carbohelicene chirality. It gathered a substantial collection of data, and a comprehensive review on the preparations of enantioenriched helicenes, either from an asymmetric synthesis or from a chiral separation. Utilizations of non-racemic helicenes and their applications will be treated in the following review (Part 3), and will not be the subject of this manuscript.

2.
ACS Omega ; 2(4): 1340-1349, 2017 Apr 30.
Artículo en Inglés | MEDLINE | ID: mdl-31457507

RESUMEN

We synthesized a novel bis-azide low-band gap cross-linkable molecule N3-[CPDT(FBTTh2)2] with wide absorption. This compound is of interest as an additive in polymer/fullerene bulk heterojunction solar cells. In addition to providing efficient thermal stabilization of the morphology, the additive can harvest additional solar light compared with pristine poly(3-hexyl thiophene) to improve the power-conversion efficiency (PCE). The additional donor material was visualized from the appearance of additional external quantum efficiency contributions between 650 and 800 nm. An open-circuit voltage increase of ∼2% compensates the decrease in the short-circuit current of ∼2% to achieve a fully thermally stabilized PCE of 3.5% after 24 h of annealing at 150 °C.

3.
Adv Mater ; 24(24): 3228-32, 2012 Jun 26.
Artículo en Inglés | MEDLINE | ID: mdl-22581758

RESUMEN

Noncontact atomic force microscopy (nc-AFM), Kelvin probe force microscopy (KPFM) and first principle calculations show that the nanostructured (001) Suzuki surface of Cd(2+) doped NaCl can be used to confine the growth of palladium clusters and functionalized brominated pentahelicene molecules into only the Suzuki regions, which contain the impurities. The Suzuki surface is an ideal model surface for nanostructuring metal clusters and molecules.


Asunto(s)
Nanopartículas del Metal/química , Nanotecnología/métodos , Impedancia Eléctrica , Halógenos/química , Modelos Moleculares , Conformación Molecular , Paladio/química , Cloruro de Sodio/química , Propiedades de Superficie
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