Novel H-Shaped Persistent Architecture Based on a Dispiro Building Block System

Abstract

[structure: see text] A novel dispiro building block, dispiro[fluorene-9,5'(7'H)-diindeno[2,1-b:1',2'-d]thiophene-7',9' '-fluorene], and its two derivatives, TBP-DSFDITF and TDOF-DSFDITF, were designed and synthesized. Because of the rigidity and orthogonality of the spiro structure, TBP-DSFDITF exhibits a well-defined H-shaped architecture, which consists of two ter(biphenyls) as the arms of the H-shape and 3,4-diphenylthiophene as the rung, connecting via completely rigid dispiro linkages with two sp(3) carbon atoms.

(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

“…[34] (Figure 1, top). [57] The (2,1-a)-indenofluorenyl core has a maximum length of 10.8, 0.3 shorter than the (1,2-b)-indenofluorenyl core. [27] Moreover, the (2,1-a)-indenofluorenyl core presents two distortions on both sides as previously observed for similar structures.…”

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

“…This phenomenon has already been observed by Huang and coworkers in investigations of related compounds. [69] Depending on the conditions, this monocoupling derivative may be formed in moderate (20 %) to high yield (50 %).…”

“…NaNO 2 Structural properties: The DSFIFs are dispiro molecules with a linear antarafacial geometry. [69] Single crystals of DSF-IFA C H T U N G T R E N N U N G (iPr) 2 were obtained by slow diffusion of hexane into a solution of the sample in CDCl 3 and were analysed by X-ray diffraction in order to elucidate its molecular structure and bulk-packing characteristics ( Figures 3 and 4).…”

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).…”