9-Fluorenone

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 3934, 1995 DOI: 10.1021/jo00118a002Synthetic Communications, 6, p. 285, 1976 DOI: 10.1080/00397917608063524

Purification Methods

Crystallise 9-fluorenone from absolute EtOH, MeOH or *benzene/pentane. [Ikezawa J Am Chem Soc 108 1589 1986.] Also recrystallise it twice from toluene and sublime it in a vacuum [Saltiel J Am Chem Soc 108 2674 1986]. It can be distilled under high vacuum. [Beilstein 7 H 465, 7 III 2330, 7 IV 1629.]

General Description

9-Fluorenone is a polycyclic aromatic ketone with a planar structure, serving as a core component in the synthesis of chiral bent cyclophanes and polyaryl derivatives. It exhibits notable optoelectronic properties, including high fluorescence quantum yields when incorporated into rigid cyclophane structures, and can be selectively functionalized through metal-catalyzed C–O bond activation for applications in materials science, such as organic light-emitting devices and liquid crystals.

Application

9-Fluorenone has been extensively used as a precursor to synthesize a variety of organic electronic materials. Some of the general examples are:Synthesis of host for the blue and green phosphorescent organic light emitting diodes (PHOLEDs).Synthesis of fluorene-based molecular motors.Synthesis of open-shell Chichibabin′s hydrocarbons as potential organic spintronic materials.It also acts as a sensitizer in the formation of picene via photosensitization of 1,2-di(1-naphthyl)ethane.

Definition

ChEBI: The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.