Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

Yang, Jye‐Shane; Yan, Jyu-Lun

doi:10.1039/b713428m

Cited by 137 publications

(66 citation statements)

References 74 publications

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“…Our results demonstrate not only an efficient and tunable control of the Brownian rotary motion of molecular rotors by photons and small structural variations [20,21] but also the potential utility of the rigid pentiptycene framework [10,22] in constructing molecular machines.…”

Section: Resultsmentioning

confidence: 92%

Pentiptycene‐Derived Light‐Driven Molecular Brakes: Substituent Effects of the Brake Component

Sun

Huang

et al. 2010

Chemistry A European J

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Five pentiptycene-derived stilbene systems (1 R; R = H, OM, NO, Pr, and Bu) have been prepared and investigated as light-driven molecular brakes that have different-sized brake components (1 H<1 OM<1 NO<1 Pr<1 Bu). At room temperature (298 K), rotation of the pentiptycene rotor is fast (k(rot)=10(8)-10(9) s(-1)) with little interaction with the brake component in the trans form ((E)-1 R), which corresponds to the brake-off state. When the brake is turned on by photoisomerization to the cis form ((Z)-1 R), the pentiptycene rotation can be arrested on the NMR spectroscopic timescale at temperatures that depend on the brake component. In the cases of (Z)-1 NO, (Z)-1 Pr, and (Z)-1 Bu, the rotation is nearly blocked (k(rot)=2-6 s(-1)) at 298 K. It is also demonstrated that the rotation is slower in [D(6)]DMSO than in CD(2)Cl(2). A linear relationship between the free energies of the rotational barrier and the steric parameter A values is present only for (Z)-1 H, (Z)-1 OM, and (Z)-1 NO, and it levels off on going from (Z)-1 NO to (Z)-1 Pr and (Z)-1 Bu. DFT calculations provide insights into the substituent effects in the rotational ground and transition states. The molar reversibility of the E-Z photoswitching is up to 46%, and both the E and Z isomers are stable under the irradiation conditions.

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Section: Resultsmentioning

confidence: 92%

Pentiptycene‐Derived Light‐Driven Molecular Brakes: Substituent Effects of the Brake Component

Sun

Huang

et al. 2010

Chemistry A European J

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“…Iptycenes are a class of structurally unique compounds that consist of a number of arene rings joined together to form the bridges of [2.2.2] bicyclic ring systems [30]. The name iptycene originated from the basic unit triptycene, which was first synthesized and named by Bartlett and coworkers in 1942 [31].…”

Section: Introductionmentioning

confidence: 99%

Triptycene poly(ether-imide)s with high solubility and optical transparency

et al. 2011

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A series of new poly(ether-imide)s containing threedimensional triptycene moieties were prepared from 1,4-bis(3,4-dicarboxyphenoxy)triptycene dianhydride with various aromatic diamines via a conventional two-stage process. The inherent viscosities of the amic acid prepolymers were in the range of 0.44~0.91 dL/g. Most of the resulting poly(ether-imide)s presented good solubility in many organic solvents and could be solution-cast into transparent and strong films. They also showed good thermal stability with glass-transition temperatures of 238~302°C and 10% weight loss temperatures in excess of 572°C. These triptycene-based poly(ether-imide)s showed enhanced optical transparency, decreased color intensity and lowered dielectric constants as compared to conventional aromatic polyimides. The poly(ether-imide)s derived from trifluoromethyl-containing bis(ether amine)s could afford highly optically transparent and almost colorless films.

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“…The tmeda diamino receptor has previously been shown to quench the PPE fluorescence by a Dexter type mechanism [22]. The pentiptycene group has a rigid three-dimensional structure, which has been widely used in conjugated polymers to prevent inter-molecular chain quenching in higher concentrations as well as in the solid state [29,38]. It is also widely accepted that this group can recognize nitrate explosives in very low concentrations in aqueous solution as well as in air [39,40].…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity

Chen

Fegley

et al. 2017

Polymers

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Fluorescent conjugated polymers (FCPs) have been explored for selective detection of metal cations with ultra-sensitivity in environmental and biological systems. Herein, a new FCP sensor, tmeda-PPpETE (poly[(pentiptycene ethynylene)-alt-(thienylene ethynylene)] with a N,N,N -trimethylethylenediamino receptor), has been designed and synthesized via Sonogashira cross-coupling reaction with the goal of improving solid state polymer sensor development. The polymer was found to be emissive at λ max~4 59 nm under UV radiation with a quantum yield of 0.119 at room temperature in THF solution. By incorporating diamino receptors and pentiptycene groups into the poly[(phenylene ethynylene)-(thiophene ethynylene)] (PPETE) backbone, the polymer showed an improved turn-off response towards copper(II) cation, with more than 99% quenching in fluorescence emission. It is capable of discriminating copper(II) cation from sixteen common cations, with a detection limit of 16.5 nM (1.04 ppb).

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Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

Cited by 137 publications

References 74 publications

Pentiptycene‐Derived Light‐Driven Molecular Brakes: Substituent Effects of the Brake Component

Pentiptycene‐Derived Light‐Driven Molecular Brakes: Substituent Effects of the Brake Component

Triptycene poly(ether-imide)s with high solubility and optical transparency

Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity

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