Synthesis of Spiro[cyclopenta[1,2-b:5,4-b′]DiThiophene-4,9′-Fluorenes] SDTF dissymmetrically functionalized

Jeux, Victorien; Dalinot, Clément; Allain, Magali; Sanguinet, Lionel; Leriche, Philippe

doi:10.1016/j.tetlet.2015.01.173

Cited by 14 publications

(20 citation statements)

References 21 publications

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“…[29] More recently, this research field has been expanded by introducing heteroaromatic spiro-skeleton cores with different optic and electronic characteristics. [12,30,31] Based on the stereoselective functionalization of the symmetrical SCPDT core, [32] we demonstrated the successful electropolymerizable design of electron donor-acceptor compounds with broad electronic absorption spectra in the visible region. [30] Our study proved that the choice of the well-known dimerizable triphenylamine (TPA) as the electron donor unit, in combination with the SCPDT core allows the electrochemical deposition of a photoelectroactive polymer.…”

Section: Introductionmentioning

confidence: 99%

“…Most of the spiro‐molecules specifically designed to electrochemically form films are based on the 9,9’‐spirobifluorene core, with applications in OLEDs, [6] electrochromic devices, [27,28] and electronic paper [29] . More recently, this research field has been expanded by introducing heteroaromatic spiro‐skeleton cores with different optic and electronic characteristics [12,30,31] . Based on the stereoselective functionalization of the symmetrical SCPDT core, [32] we demonstrated the successful electropolymerizable design of electron donor‐acceptor compounds with broad electronic absorption spectra in the visible region [30] .…”

Section: Introductionmentioning

confidence: 99%

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Electron Donor‐Acceptor Spirobi[cyclopenta[2,1‐b : 3,4‐b′]dithiophene] Derivatives as Precursors of Electrodeposited Regioregular Thiophene‐based Polymers

Minudri

Orlandi²,

Cavazzini³

et al. 2020

Eur J Org Chem

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Dedicated to Professor Franco Cozzi on the occasion of his 70th birthday. A series of conjugation extended push-pull derivatives of 4,4'spirobi[cyclopenta[2,1-b : 3,4-b']dithiophene] were synthesized and fully characterized, in which each perpendicularly aligned cyclopenta[2,1-b : 3,4-b']dithiophene features a pendant dicyanovinylene as an electron acceptor and a thiophene as an electron donor. The electrochemical and photophysical properties of the new molecules, which differ from each other for the presence and/or location of an additional n-hexyl chain on the pendant thiophene unit, were investigated, as well as their susceptibility to electrochemical polymerization. The substitution arrangement of the monomers was found to exert significant influence on the outcome of the electropolymerization process and on the optoelectronic properties and morphological film characteristics of the new regioregular materials obtained.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electron Donor‐Acceptor Spirobi[cyclopenta[2,1‐b : 3,4‐b′]dithiophene] Derivatives as Precursors of Electrodeposited Regioregular Thiophene‐based Polymers

Minudri

Orlandi²,

Cavazzini³

et al. 2020

Eur J Org Chem

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“…19 Moreover, the prefunctionalization of terminal positions may also in some cases partially avoid the unprotected step. 20 Nevertheless, in all these cases, the number of synthetic steps and overall yields may constitute an obstacle to the development of further devices.…”

Section: Introductionmentioning

confidence: 99%

Prediction of the Synthesis of Spiro Derivatives by Double Intramolecular Aromatic Electrophilic Substitution Using Reactivity Indices

et al. 2019

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The synthesis of heterocyclic spirobifluorene (SBF) analogs generally requires long and complicated synthetic pathways. Despite this synthetic effort, such structural modification allows the (opto)electronic properties of this remarkable three-dimensional node to be tuned especially for molecular electronic applications. For this reason, the development of a simple, robust, and efficient synthetic methodology to introduce various heterocycles in place of classical phenyl rings in the spirofluorene motif is highly and timely desirable. In this context, we describe herein our efforts to develop a straightforward and efficient synthesis leading to replacement of 2 phenyl rings by various heterocycles in spiro compounds from 2,2′-dibromobenzophenone. As the same procedure to form fully heterocyclic compounds failed, an original theoretical approach based mainly on the uncommon Fukui dual function was developed in order to determine clearly the limitation of this strategy and provide an efficient predictive tool. Indeed, such calculation allows prediction of the thermodynamic and kinetic aspects of the synthesis of spiro derivatives using a double aromatic electrophilic substitution. If this procedure reproduces well our experimental results focused on (heterocyclic) SBF compounds, it can be certainly adapted and generalized to other intramolecular substitutions.

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“…[8] Many alternatives are thus developed, most of which contain a single spiro core, as shown in Figure 1. [9][10][11][12][13][14][15][16][17] These spiro-type compounds can achieve a high glass transition temperature (T g ) thanks to the sp 3 -hybridized carbon atom at the junction of the two molecular halves, which leads to a highly sterically demanding structure with the perpendicular arrangement. This molecular arrangement induces rigidity in the molecule, effectively impeding crystallization below the T g and enhancing the stability of the amorphous state for the formation of good films.…”

Section: Introductionmentioning

confidence: 99%

“…However, the high cost, low charge carrier mobility, and tendency to aggregation in the film after doping significantly limit its suitability for large‐scale fabrication of PSCs . Many alternatives are thus developed, most of which contain a single spiro core, as shown in Figure . These spiro‐type compounds can achieve a high glass transition temperature ( T g ) thanks to the sp 3 ‐hybridized carbon atom at the junction of the two molecular halves, which leads to a highly sterically demanding structure with the perpendicular arrangement.…”

Section: Introductionmentioning

confidence: 99%

A Dispiro‐Type Fluorene‐Indenofluorene‐Centered Hole Transporting Material for Efficient Planar Perovskite Solar Cells

Zhang

Wang

et al. 2018

Solar RRL

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A novel dispiro[fluorene‐indenofluorene]‐based compound, dispiro‐OBuTAD (shortened as Dispiro) with a 3π‐2 spiro core is designed and synthesized as a hole transporting material (HTM) for perovskite solar cells (PSCs). The Dispiro with two spiro centers shows rigid ladder‐type structure, great steric hindrance, and reduced molecular symmetry, which favor good thermal stability and homogeneous film morphology. Devices with Dispiro as HTM afford a high power conversion efficiency amounting to 18.46% in MAPbI3‐based planar PSCs, which is higher than the value (17.82%) of the well‐known spiro‐OMeTAD‐based devices. The Dispiro can form amorphous homogeneous films with improved hole mobility and enhanced hole extraction from perovskite to HTM, resulting in high performance of Dispiro‐based PSCs. This work provides the first example of fluorene‐indenofluorene‐centered dispiro‐type HTM for PSC application, suggesting a promising approach to design HTMs by increasing the spiro center.

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Synthesis of Spiro[cyclopenta[1,2-b:5,4-b′]DiThiophene-4,9′-Fluorenes] SDTF dissymmetrically functionalized

Cited by 14 publications

References 21 publications

Electron Donor‐Acceptor Spirobi[cyclopenta[2,1‐b : 3,4‐b′]dithiophene] Derivatives as Precursors of Electrodeposited Regioregular Thiophene‐based Polymers

Electron Donor‐Acceptor Spirobi[cyclopenta[2,1‐b : 3,4‐b′]dithiophene] Derivatives as Precursors of Electrodeposited Regioregular Thiophene‐based Polymers

Prediction of the Synthesis of Spiro Derivatives by Double Intramolecular Aromatic Electrophilic Substitution Using Reactivity Indices

A Dispiro‐Type Fluorene‐Indenofluorene‐Centered Hole Transporting Material for Efficient Planar Perovskite Solar Cells

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