Mesomorphism of Hybrid Siloxane-Triphenylene Star-Shaped Oligomers

Zelcer, Andrés; Donnio, Bertrand; Bourgogne, Cyril; Cukiernik, Fabio Daniel; Guillon, Daniel

doi:10.1021/cm062949b

Cited by 110 publications

(53 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…31 Only one example of columnar liquid crystals of triphenylene derivatives bearing six oligosiloxane chains has been reported. 32 For side chain polymers, high hole mobility was observed in a nanosegregated smectic phase in which rigid side chain mesogenic terthiophene units and liquid-like polysiloxane chains were microscopically separated. 33 Perylene tetracarboxylic bisimide (PTCBI) derivatives are typical n-type organic semiconductors.…”

Section: Nanosegregated Columnar Phases Of Perylene Bisimide Derivatimentioning

confidence: 99%

Integration of electro-active π-conjugated units in nanosegregated liquid-crystalline phases

Funahashi

2016

Polym J

View full text Add to dashboard Cite

Unlike conventional liquid crystals bearing alkyl chains, perylene tetracarboxylic bisimide (PTCBI) derivatives bearing oligosiloxane moieties were synthesized. The oligosiloxane moieties are bulky and have a tendency to form a liquid-like conformation due to the low rotation potential of Si-O bonds. The PTCBI derivatives bearing oligosiloxane chains exhibit the columnar phase at room temperature. They are soluble in various organic solvents, and thin films can be produced by a spin-coating method. In the columnar phase, crystal-like π-stacks are surrounded by a liquid-like mantle consisting of the oligosiloxane moieties of the PTCBI derivatives, resulting in efficient electron transport. Even the PTCBI derivatives bearing polymerizable cyclotetrasiloxane rings show the liquid-crystalline (LC) phases at room temperature. The spin-coated films of the LC PTCBI derivatives with cyclotetrasiloxane rings can be polymerized and insolubilized by exposure to the vapors of trifluoromethanesulfonic acid. PTCBI derivatives bearing oligosiloxane moieties and a triethylene oxide chain coordinated to ionic species exhibit a dimeric lamellar phase in which ion-conductive sublayers and electron-transporting π-stacks are separately self-organized. Phenylterthiophene derivatives bearing oligosiloxane moieties show a ferroelectric smectic C* phase in which the anomalous photovoltaic effect is observed.

show abstract

Section: Nanosegregated Columnar Phases Of Perylene Bisimide Derivatimentioning

confidence: 99%

Integration of electro-active π-conjugated units in nanosegregated liquid-crystalline phases

Funahashi

2016

Polym J

View full text Add to dashboard Cite

show abstract

“…In particular, Si‐containing π‐conjugated macrocycles possessing the interesting properties, including excellent heat, radiation, chemical resistance, film‐forming ability and low dielectric constants. Therefore, they have been investigated as potential materials for semiconductors, light emitters, and photovoltaic systems …”

Section: Figurementioning

confidence: 99%

Synthesis and Cyclization‐Induced Charge Transfer of Rectangular Bisterthiophenesiloxanes

Tashiro

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

Cyclization‐modified terthiophene displays the change of emission behavior from locally excited (LE) to the intramolecular charge transfer (ICT) state. The rectangular bisterthiophenesiloxanes (DSiTh) was successfully prepared by π–π‐stacking‐aided hydrogen‐bonding interactions. Cyclization‐induced ICT in DSiTh could be observed, which was confirmed by absorption spectra, fluorescence spectra, and quantum chemistry analysis. The cyclization produces a strong intramolecular electron redistribution of a highly packed π‐conjugated terthiophene. Thus, a distinctive variation of the dipole moment and a through‐space ICT happen.

show abstract

“…Side chain polymers based on discotic mesogens have been much less explored and it concerns in particular systems based on flexible, linear polysiloxanes with triphenylene moieties. Only a limited number of star shaped oligomers [12,19,20] and side chain systems [21][22][23] has been explored so far, although these polymers may also have an increased tendency to form columnar mesophases which might help to obtain thin layers with high molecular order.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermotropic behavior of side chain polysiloxane bearing triphenylene moiety

Makowski¹,

Ganicz²,

Zaja̧czkowski³

et al. 2015

Express Polym. Lett.

View full text Add to dashboard Cite

Abstract. Side chain discotic polysiloxane with 2,3,6,7-tetrakis(hexyloxy)-10-methoxytriphenylene-11-undecanoate moieties is synthesized by hydrosilylation reaction. The phase behavior and thermooptical properties of the polysiloxane and the side chain precursor 2,3,6,7-tetrakis(hexyloxy)-10-methoxytriphenylene-11-undecanoate are examined by polarizing optical microscopy, thermooptical analysis, differential scanning calorimetry and wide angle X-ray scattering studies. A columnar planar alignment of LC in the layers has been determined. The pronounced alignment makes this polymer a promising material for application in optoelectronic devices. The differences in phase transitions and morphology between the triphenylene precursor and the discotic polysiloxane are discussed.

show abstract

Mesomorphism of Hybrid Siloxane-Triphenylene Star-Shaped Oligomers

Cited by 110 publications

References 62 publications

Integration of electro-active π-conjugated units in nanosegregated liquid-crystalline phases

Integration of electro-active π-conjugated units in nanosegregated liquid-crystalline phases

Synthesis and Cyclization‐Induced Charge Transfer of Rectangular Bisterthiophenesiloxanes

Synthesis and thermotropic behavior of side chain polysiloxane bearing triphenylene moiety

Contact Info

Product

Resources

About