Fluorescent carborane–vinylstilbene functionalised octasilsesquioxanes: synthesis, structural, thermal and photophysical properties

Abstract

The functionalization of POSS with vinylstilbene–carborane moieties leads to tunable fluorescent hybrids with an outstanding thermal stability.

Photoluminescence in m-carborane–anthracene triads: a combined experimental and computational study

“…Icosahedral carborane clusters, in particular dicarba-closo-dodecaboranes (C2B10H12), 1-10 are highly chemical and thermally stable boron clusters, [11][12][13] characterized for their threedimensional (3D) structure with electrons' delocalization inside the cage. 14,15 These boron clusters possess a highly polarisable σ-aromatic character and interact electronically with πconjugated systems.…”

“…But more interestingly, the fluorescence efficiency can be tailored by changing the substituent at the adjacent Cc position, which may cause either an enhancement of the emission quantum yield or a total fluorescence quenching in the case of aromatic substituents. [11][12][13][65][66][67][68][69] Anthracene is a very well-studied -conjugate system easy to functionalize and with remarkable intrinsic photophysical, photochemical and chemical properties, which make it and its derivatives ideal molecules to construct fluorophores, fluorescent probes, organic light-emitting transistors, among others. 70,71 Throughout the last years, some carboranyl-functionalized anthracene derivatives have been reported and their photoluminescence behaviour explored.…”

Carborane‐BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling

“…Littke and Fu described in 2001 the Pd 2 (dba) 3 /Pd(P( t Bu) 3 ) 2 catalytic system in the presence of dicyclohexylmethylamine (Cy 2 NMe) as an effective tool for Heck reactions of aryl chlorides and aryl bromides, suitable for both harsh and mild conditions . The unusual effectiveness of the base, which was proven to provide a more active catalyst compared to other bases (such as Cs 2 CO 3 ), also made this versatile procedure efficient to introduce a variety of functional groups either on brominated and iodinated silicate cages (possessing similar characteristics to the carborane cluster) and on the carboranyl substrates of our interest –…”

“…Since our seminal work in 2007, in which the first example of fluorescent molecules containing carboranyl moieties was reported, our group, and others have developed new fluorescent materials incorporating carboranes. As a result, the interest in studying the photoluminescent (PL) properties of these compounds in view of new applications has noticeably increased.…”

“…As part of our studies aimed at tagging biological relevant compounds using fluorescent probes for live cell‐imaging applications, we exploited the excellent photo‐features of BODIPYs as optical probes and we recently reported the optimization of a Heck coupling‐reaction on an asymmetric aza‐BODIPY core . Likewise, styrene‐containing carborane derivatives have demonstrated to be excellent starting molecules to achieve different fluorescent materials through a Heck coupling reaction –. Therefore, we envisaged that these derivatives might represent a very suitable coupling partner for Heck reactions with halogenated BODIPY fluorophores and their aza‐analogues.…”