The Role of Side‐Arms for Supramolecular Affinity Materials Based on 9,9′‐Spirobifluorenes

Pyka, Isabella; Nikl, Joachim; Schollmeyer, Dieter; Waldvogel, Siegfried R.

doi:10.1002/ejoc.201700758

Cited by 5 publications

(2 citation statements)

References 52 publications

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“…Examples of differently substituted SBF‐based molecules. 4,4′,4″,4″′‐(9,9′spirobi[fluorene]‐2,2′,7,7′‐tetrayl)tetrabenzoic acid ( 1 ) and its Cu‐based MOF, [ 8 ] spiro‐cycloparaphenylene ( 2 ) with 16 phenyl units (CCDC 1 961 179), [ 11 ] (S,S,S,S)‐cyclo[3]spirobifluorenylene (CCDC 1 991 410) ( 3 ), [ 14 ] (S,S,S,S)‐cyclo[4]spirobifluorenylene (CCDC 1 991 411) ( 4 ), [ 14 ] PdCl 2 (SBF(PPh 2 ) 2 ( 5 ) (CCDC 256 882), [ 13 ] spiro[fluorene‐9,15′‐indeno[2,1‐ g ]‐ chrysene] ( 6 ) (CCDC 1 557 124), [ 18 ] spirobi[indeno[2,1‐ b ]fluorene]‐12,12'‐diylidene)dimalononitrile ( 7) (CCDC 1 035 932), [ 19 ] 2,3,8,9,14,15,20,21‐Octamethyl‐tetrapyrazino[2,3‐b:2′,3′‐h:2″,3″‐b′:2″′,3″′‐h′]‐9,9′‐spirobifluorene ( 8 ) (CCDC 15 428 680), [ 21 ] 3,3',9,9'‐Tetra‐tert‐butyl‐6,6′‐spirobi[cyclopenta[2,1‐ b :3,4‐ b′]difluorene]‐12,12′,15,15′‐tetraone ( 9 ) (CCDC 1 408 336). [ 20 ] …”

Section: Introductionmentioning

confidence: 99%

Spirobifluorene Dimers: Understanding How The Molecular Assemblies Drive The Electronic Properties

Poriel

Quinton

Lucas

et al. 2021

Adv Funct Materials

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Spirobifluorene (SBF) is one of the most important scaffolds used in the design of organic semi‐conductors (OSCs) for electronics. In recent years, among all the structures developed for these applications, SBF dimers have been highlighted due to their great potential in thermally activated delayed fluorescence and in phosphorescent organic light‐emitting diodes. Attaching two SBF units generate 10 dimers, each possessing its own structural specificity, which in turn drives its electronic properties. These ten SBF dimers are gathered herein. Understanding how the molecular assembly determines the electronic properties has been one of the pillars of organic electronics. This is the goal of this article. As positional isomerism is a key tool to design OSCs, defining the design guidelines for the SBF scaffold appears of interest for the future of this building block. Herein, the importance of the two main parameters involved in the electrochemical and photophysical properties, namely the nature of the phenyl linkages and the steric congestion between the two SBF units is discussed. The combination of these two parameters drives the electronic properties but their respective weight is different as a function of the regioisomer involved or of the property considered (frontier orbitals energy level, absorption, fluorescence, phosphorescence).

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Section: Introductionmentioning

confidence: 99%

Spirobifluorene Dimers: Understanding How The Molecular Assemblies Drive The Electronic Properties

Poriel

Quinton

Lucas

et al. 2021

Adv Funct Materials

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“…Diethylaluminum chloride, ethylaluminum sesquichloride, and di- n -butylmagnesium (Aldrich) were used without further purification. (±)-Camphorquinone was obtained by the method described in [ 30 ]. The preparation of the ligands L1 and L2 followed the procedure described in [ 31 ]; their properties corresponded to the literature data.…”

Section: Methodsmentioning

confidence: 99%

New Titanium(IV)-Alkoxide Complexes Bearing Bidentate OO Ligand with the Camphyl Linker as Catalysts for High-Temperature Ethylene Polymerization and Ethylene/1-Octene Copolymerization

et al. 2022

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In order to increase the thermal stability of olefin polymerization precatalysts, new titanium(IV) complexes with diolate ligands differing in the degree of steric hindrances were synthesized from readily available precursor (±)camphor. The structures of the complexes 1–2 were established by X-ray diffraction. Complexes 1-4 in the presence of an activator {EtnAlCl3-n + Bu2Mg} catalyzed the synthesis of UHMWPE with an Mv up to 10 million and a productivity of up to 3300 kg/molTi·atm·h. The obtained polymers are obviously characterized by a low density of macromolecular entanglement, which makes it possible to use the solid-phase method for their processing. The mechanical characteristics of the oriented UHMWPE films had a breaking strength up to 2.7 GPa and an elastic modulus of up to 151 GPa. The precatalysts 1-4 were also active in ethylene/1-octene copolymerization. The comonomer content was in the range of 1.4–4.6 mol%. The use of a rigid linker and an increase in the steric load of the diolate complexes ensured the thermal stability of the catalytic system in the range of 50–70 °C.

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One‐Pot Synthesis to Quinone‐Based Diaza[3.3]cyclophanes

2017

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A simple one-pot synthesis to [3.3]cyclophanes that involves quinone moieties was found. The protocol tolerates a variety of amines that include aliphatic and aromatic structures with different functional groups, such as hydroxy groups, amides, and terminal double and triple bonds. The straightforward synthesis can be performed by a twofold N-alkylation reaction with 2,5-bis(bromomethyl)-3,6-dimethyl-1,4-benzoquin-

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The Role of Side‐Arms for Supramolecular Affinity Materials Based on 9,9′‐Spirobifluorenes

Cited by 5 publications

References 52 publications

Spirobifluorene Dimers: Understanding How The Molecular Assemblies Drive The Electronic Properties

Spirobifluorene Dimers: Understanding How The Molecular Assemblies Drive The Electronic Properties

New Titanium(IV)-Alkoxide Complexes Bearing Bidentate OO Ligand with the Camphyl Linker as Catalysts for High-Temperature Ethylene Polymerization and Ethylene/1-Octene Copolymerization

One‐Pot Synthesis to Quinone‐Based Diaza[3.3]cyclophanes

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