Quaterthiophene-based dimers containing an ethylene bridge: molecular design, synthesis, and optoelectronic properties

Jenart, Maud; Niebel, Claude; Balandier, Jean‐Yves; Leroy, Julie; Mignolet, Alix; Stas, Sara; Vooren, Antoine Van; Cornil, Jérôme; Geerts, Yves

doi:10.1016/j.tet.2011.10.020

Cited by 9 publications

(11 citation statements)

References 38 publications

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“…Even though short σ-covalent bridges between π-conjugated systems do break the conjugation, they do not necessarily break the electronic communication because under certain geometric constraints through-bond coupling could be possible. [ 12 ] Besides avoiding these additional coupling effects, one has to ensure that the fl exible linker is long enough to allow polymer chain folding. Previous reports on monodisperse alkyl chains suggested that six to ten methylene groups are sufficient to allow chain folding, which is why a hexyl linker was introduced between two thiophene units.…”

Section: Resultsmentioning

confidence: 99%

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Non‐Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance

Schroeder

Chiu

et al. 2016

Adv Elect Materials

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Keywords: semiconducting polymer, glass transition temperature, all-polymer solar cell, organic field effect transistor, isoindigo Semiconducting polymers, in contrast to inorganic silicon, are solution processable and can potentially be printed cost efficiently on flexible large-area substrates. However to do so it is of paramount importance to formulate the polymeric semiconductors into inks with specific viscosities. Herein we present the synthesis of a new highly soluble isoindigo monomer and its incorporation into low bandgap semiconducting polymers. Non-conjugated flexible linkers are introduced into the conjugated backbone in order to modulate the materials processability.The viscoelastic properties of the new polymers are studied in detail by means of rheometry and dynamical mechanical analysis (DMA). The solution viscosity is directly proportional to the content of non-conjugated linkers in the polymer backbone. In organic field-effect transistors (OFETs) maximum hole mobilities of 1. oligomer side chains to enhance the solubility. [1,2] Even though these approaches have proven to be extremely successful, the introduction of a large number of long electrically insulating side chains may reduce the inter-chain charge transport as well as hinder the charge transfer from donor to acceptor in organic photovoltaic devices. [3] Choosing the right combination between side chain structure, length and density along the conjugated backbone is non-trivial and can quickly lead to adverse effects, making the screening process very time consuming.An alternative approach to solubilising side chains is to increase the disorder along the conjugated backbone and to disturb the molecular aggregation, thus facilitating the solution processability. Increasing the energetic disorder within a conjugated polymer chain can be achieved by introducing large rotational angles along the backbone by homo-coupling six-membered aromatic rings (i.e. biphenyl, bipyridine, etc.). Or alternatively by introducing sterically hindered head-to-head couplings into the backbone. In both cases the steric hindrance will lead to an increase in rotational 3 disorder along the polymer chain and reduced molecular aggregation in solution. [4] Unfortunately, the increase in rotational disorder with these approaches is not limited to the solution phase, but also translates into the solid state. Because the steric hindrance is 'locked' into the molecular structure of the polymer backbone, it is irreversible and leads to poor solid state order and inferior electronic properties. A less explored approach to increase energetic disorder along the polymer chain is to introduce non-conjugated, more flexible segments into the backbone. Introducing flexible linkers increases the polymer's solubility, but crucially should also allow the polymer chain to pack densely in solid state because the backbone rigidity is not perturbed by sterically induced disorder.In this paper we investigate how the introduction of flexible linkers into the conjugated backbone influ...

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Section: Resultsmentioning

confidence: 99%

“…[12] Besides avoiding these additional coupling effects, one has to ensure that the flexible linker is long enough to allow polymer chain folding. Previous reports on monodisperse alkyl chains suggested that six to ten methylene groups are sufficient to allow chain folding, which is why a hexyl linker was introduced between two thiophene units.…”

mentioning

confidence: 99%

Non‐Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance

Schroeder

Chiu

et al. 2016

Adv Elect Materials

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“…The photoluminescence properties of DHQT and derivatives have previously been reported in the literature [44][45][46].…”

Section: Photoluminescence Propertiesmentioning

confidence: 94%

“…Among the variety of oligomers used in the synthesis of semi-conducting materials, oligothiophenes have received a high interest, mainly due to the π-electron delocalisation, high polarisability of sulphur atoms and supramolecular organisation coupled with synthetic accessibility [12][13][14]. In particular, alkyl derivatives of oligothiophenes, such as terthiophene and quaterthiophene, constitute an interesting class of electroactive polymers with potential application in organic electronics [15] that can be used as components of active layers for application in electronic devices such as Organic Field Effect Transistors (OFETs) [16,17], photovoltaic cells [18] and electrochromic devices [19].…”

Section: Introductionmentioning

confidence: 99%

Copolymerisation as a way to enhance the electrochromic properties of an alkylthiophene oligomer and a pyrrole derivative: copolymer of 3,3′″ dihexyl-2,2′:5′,2″:5″,2′″-quaterthiophene with (R)-(-)-3-(1-pyrrolyl)propyl-N-(3,5-dinitrobenzoyl)-α-phenylglycinate

Silva

Nogueira

Santos

et al. 2015

Solar Energy Materials and Solar Cells

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“…The choice of terthiophene as the fluorescent group lies in its interesting optical and electronic properties that have been verified applicable in many fields. 7,[21][22][23][24][25] Moreover, the oligothiophenes exhibit unique versatile emissions depending on the intermolecular distance. [26][27][28] If the distance between the terthiophene groups is around [3][4] A, p-p stacking may occur which allows a blue emission; 27,29 when the distance is increased to [4][5][6][7] A, one may obtain green emissions from the excimers.…”

Section: Introductionmentioning

confidence: 99%

A surfactant-assisted unimolecular platform for multicolor emissions

et al. 2012

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We present here a simple molecular assembly approach to multicolor emissions based on a unimolecular platform of a terthiophene-containing amphiphile TTC4L. The amphiphiles selfassemble into vesicles in solution which exhibit a blue emission. Upon controlling the distance between the fluorescent terthiophene groups by transformation of the self-assembly of TTC4L molecules into their co-assembly with surfactants, the color of the emissions can be continuously tailored which covers most of the visible region. Since the multi-colors were obtained without any structural modification on the fluorescent molecules, we have demonstrated a real unimolecular platform for fabricating multicolor emissions. In contrast, only dual emissions can be obtained from TTC4L using host-guest chemistry. As a simple approach of 'tunable emissions', this surfactant-assisted unimolecular platform opens a new vista for the application of molecular assemblies in advanced light emitting materials.

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Quaterthiophene-based dimers containing an ethylene bridge: molecular design, synthesis, and optoelectronic properties

Cited by 9 publications

References 38 publications

Non‐Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance

Non‐Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance

Copolymerisation as a way to enhance the electrochromic properties of an alkylthiophene oligomer and a pyrrole derivative: copolymer of 3,3′″ dihexyl-2,2′:5′,2″:5″,2′″-quaterthiophene with (R)-(-)-3-(1-pyrrolyl)propyl-N-(3,5-dinitrobenzoyl)-α-phenylglycinate

A surfactant-assisted unimolecular platform for multicolor emissions

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