Dispirofluorene-indenofluorene (DSFIF):  Synthesis, Electrochemical, and Optical Properties of a Promising New Family of Luminescent Materials

Abstract

[reaction: see text] A series of new dispiro[fluorene-9',6,9' ',12-indeno[1,2b]fluorenes] (DSFIFs) that combine indenofluorene (IF) and spirobifluorene (SBF) architectural specificities have been prepared. Their anodic oxidations lead to the formation of nonsoluble transparent polymers. The photophysical and electrochemical properties of these new molecules have been evaluated for further blue OLED applications.

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

“…To avoid long and sophisticated multistep syntheses, the first method we developed involved original arylboronic acids bearing a triazene moiety in the ortho position readily convertible into iodide (Scheme 2, route 1). [52,53] 2-Iodoaniline (1) was diazotised by conventional means [60] and reacted in situ with pyrrolidine under basic conditions. The resulting o-iodoaryltriazene 2 was then converted into the corresponding boronic acid 3 by a lithiation/borylation sequence involving n-butyllithium and trimethylborate followed by hydrolytic workup.…”

“…In this work, as a development to our preliminary note, [53] we first report our synthetic investigations and a new straightforward route to the diiodoterphenyl as key building block in the synthesis of DSF-IFs. The thermal, structural, photophysical and electrochemical properties of these molecules will be discussed, together with their first application in electroluminescent devices.…”

Structure–property relationship of 4-substituted-spirobifluorenes as hosts for phosphorescent organic light emitting diodes: an overview

“…6,7 From a more fundamental point of view, the orthogonal configuration induced by the spiro carbon also allows to design shape persistent molecules with specific arrangements, which in turn has peculiar electronic consequences. 3,4,[8][9][10][11][12][13][14][15] In addition, the application field of the SBF scaffold is not only restricted to electronics and SBF has also found many other appealing applications as chiral ligand, [16][17][18][19] electropolymerizable building block, [20][21][22][23][24][25][26] homogeneous 27 and heterogeneous 23-25, 28, 29 catalysts or as building unit in coordination polymers, [30][31][32] clearly showing the versatility of this fragment. Sixteen positions of substitutions are available on the SBF backbone, eight on each fluorene unit (figure 1).…”

Preparation of Novel Fused Ring Spiro[benzotetraphene-fluorene] Derivatives and Application for Deep-Blue Host Materials

“…6 Representative organic spiro materials as blue light-emitting materials include spirobifluorenes containing anthracene, pyrene, aromatic amines, spirofluorene, and their oligomers. [7][8][9][10][11][12][13][14][15][16][17][18][19] Spiro-type host and dopant materials containing benzofluorene as OLED fluorescent materials have recently received a great deal of attention because they provide a variety of substituents on the spiro[benzo[c]fluorene-7,9'-fluorene] (SBFF) due to their asymmetric spiro core structure with naphthalene, phenyl rings of spiro molecules, and conjugation controlled OLED host materials, as shown in Scheme 1. [20][21][22][23][24] More recently, spiro[benzo [de]anthracene-7,9'-fluorene] (SBAF) derivatives were prepared and adopted to OLED host and dopant materials.…”