Synthesis and photophysical properties of highly emissive compounds containing a dibenzosilole core

A series of new rigid rod-like molecules consisting of a dibenzosilole core, ethynylene linkages, and different aryl end-groups has been synthesized by palladium-catalyzed Sonogashira cross-coupling reactions. These compounds exhibit intense blue to green emissions with high quantum efficiencies and good thermal stabilities.     

Conjugated polymer consisting of dibenzosilole and quinoxaline as donor materials for organic photovoltaics

The new D–A type polymers poly(dibenzosilole-diphenylquinoxaline) (PSiPDTQ) and dibenzosilole-dibenzophenazine) (PSiFDTQ), both of which adopted benzosilole as a donor, were polymerized through a Suzuki coupling reaction. PSiPDTQ and PSiFDTQ were able to be dissolved in organic solvents and exhibited high thermal stability. Due to the appropriate LUMO energy levels, an effective charge transport was observed in PSiPDTQ and PSiFDTQ. According to X-ray diffraction measurements, a single broad diffraction peak was detected at approximately 20.5°. The π–π stacking distances (d_π) for PSiPDTQ and PSiFDTQ were 4.4 and 4.3 Å, respectively. When PSiPDTQ and PC₇₁BM were blended in a 1:3 ratio and used as the active layer in a solar cell, the resulting V_oc, J_sc, FF and PCE were 0.89 V, 5.1 mA/cm², 30.2% and 1.4%, respectively. For solar cells using a 1:6 ratio of PSiFDTQ to PC₇₁BM, the resulting V_oc, J_sc, FF and PCE were 0.98 V, 3 mA/cm², 52.8% and 1.6%, respectively. In addition, for a PSiPDTQ and PC₇₁BM blended film (1:3 ratio) with an additional layer of PFN, the PCE of the resulting solar cells was improved (relative to solar cells without PFN) to 2.1% due to the interfacial adhesion of PFN.     

One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis

Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o ‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group tolerance. Furthermore, double π‐extension reactions of 1,4‐bis(phenylethynyl)benzene and diphenyl‐1,3‐butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes.     

Synthesis and photophysical properties of poly(aryleneethynylene)s containing dibenzosilole unit

A series of poly(aryleneethynylene)s containing dibenzosilole unit has been synthesized by palladium-catalyzed Sonogashira cross-coupling reactions with 2,7-diethynyl-9,9-dihexyl-3,6-dimethoxy-9H-dibenzosilole(4) as the key monomer.Their photophysical properties in solution were investigated.All of the polymers showed intense fluorescence with high quantum efficiencies.     

Construction of Chiral Tetraorganosilicons by Tandem Desymmetrization of Silacyclobutanes/Intermolecular Dehydrogenative Silylation

We report a method to construct chiral tetraorganosilicons by tandem silacyclobutane (SCB) desymmetrization–dehydrogenative silylations. A wide array of dibenzosiloles with stereogenic quaternary silicon centers were obtained in good yields and enantioselectivities up to 93 % ee . Chiral TMS‐segphos was found to be a superior ligand in terms of reactivity and enantioselectivity.