Synthesis of Dibenzo[hi,st]ovalene and Its Amplified Spontaneous Emission in a Polystyrene Matrix

Abstract

A large number of graphene molecules, or large polycyclic aromatic hydrocarbons (PAHs), have been synthesized and display various optoelectronic properties. Nevertheless, their potential for application in photonics has remained largely unexplored. Herein, we describe the synthesis of a highly luminescent and stable graphene molecule, namely a substituted dibenzo[hi,st]ovalene (DBO 1), with zigzag edges and elucidate its promising optical‐gain properties by means of ultrafast transient absorption spectroscopy. Upon incorporation of DBO into an inert polystyrene matrix, amplified stimulated emission can be observed with a relatively low power threshold (ca. 60 μJ cm−2), thus highlighting its high potential for lasing applications.

Nanographenes: Ultrastable, Switchable, and Bright Probes for Super‐Resolution Microscopy

“…These properties include 1) size, 2) absorption and emission spectra, 3) duty cycle (fraction of time a molecule resides in its fluorescent state), and 4) photon number (detected photons per switching event). Figure a,b shows the chemical structures and spectra of DBOV‐Mes , dibenzo[ hi , st ]ovalene (DBOV) with two mesityl (Mes) groups, and GM‐C60 with alkyl side chains. DBOV‐Mes (GM‐C38) and GM‐C60 consist of 38 and 60 sp 2 ‐hybridized carbons in their aromatic cores, both with an approximate size of 1 to 2 nm.…”

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

“…One way to gain extra stability in zPAHs is to disrupt the zigzag pattern at the edge of the molecule. Using this strategy, Narita and coworkers synthesized ovalene derivatives (compounds 21 and 22 , Figure ) whose upper and lower edges have a zigzag topology while the left and right edges are of armchair type . Band gap values as low as 1.91 eV have been obtained with a strong, sharp absorption peaking at ca .…”

Nanographene: ultrastabile, schaltbare und helle Sonden für die hochauflösende Mikroskopie

“…Zu diesen Eigenschaften gehören 1) Größe, 2) Absorptions‐ und Emissionsspektren, 3) Leuchtdauern (Bruchteil der Zeit, in dem sich ein Molekül in seinem fluoreszierenden Zustand befindet) und 4) Photonenzahl (erfasste Photonen pro Schaltereignis). Abbildung a,b zeigt die chemischen Strukturen und Spektren von DBOV‐Mes (Dibenzo[ hi , st ]ovalen (DBOV) mit zwei Mesityl(Mes)‐Gruppen) und GM‐C60 mit Alkyl‐Seitenketten. DBOV‐Mes ( GM‐C38 ) und GM‐C60 bestehen aus 38 bzw.…”