Physical Properties of Thiophene<sup>1</sup>

Fawcett, Frank S.; Rasmussen, Herbert E.

doi:10.1021/ja01226a026

Cited by 47 publications

(12 citation statements)

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“…There is a broad band at the lower wavelength spectral region (<400 nm) that could be associated with the absorption of the thiophene heterocycle. 81,82 This band is more pronounced and red-shifted for the fused M1F dimer, which complies also with its rigid structure. 76 The fused M1F dimer had a larger solvatochromic shift relative to the unfused M1 dimer, indicating a greater effect of solvent polarity on its photophysical properties (Figure S1).…”

Section: ■ Resultssupporting

confidence: 65%

Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

et al. 2021

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N-Annulated perylene diimide (PDI) dimers offer added advantages over conventional (non-annulated) dimers or S/ Se-annulated dimers due to the two extra positions of functionalization that they provide, which can be used to improve the solution processability, impact the packing and self-assembly of the molecules in thin films, and tune the absorption and emission energies. In this work about N-annulated thiophene π-bridged PDI dimers, we present a unique strategy to use ring-fusion to highlight the different excited state decay pathways taking place in these systems. Two analogous N-annulated PDI dimers were investigated, whose structures show a rotatable single-bond connection with the thiophene π-bridge (M1) relative to a rigid fused π-bridge connection (M1F). We show that ring-fusion of the M1F dimeric system yields ultrafast intramolecular charge transfer and charge separation, relative to the unfused dimer. For M1Fthe fused N-annulated thiophene π-bridged PDI dimerthe charge separation rate increased by over 1 order of magnitude compared to the charge separation rate of M1. Also, ring-fusion opened up the triplet excited state deactivation pathway that was not present in the unfused dimer. The rate of triplet production was shown to be dependent on the polarity of the solvent environment for the fused M1F dimer. We were able to track the respective excited state species (PDI*, PDI •+ , PDI •− , PDI 3 *) generated upon photoexcitation, using both femtosecond and nanosecond time resolution to obtain a complete description of the entire activation and deactivation pathways. Nonlinear two-photon absorption measurement was used to provide insights into the excited state charge transfer properties of the compounds. The results were able to show that ring fusion leads to increased electronic coupling between the PDI units of the dimer, which in turn led to an increased charge separation rate and dictated the production of long-lived triplet species. Also, this detailed study points out that ring fusion in Nannulated PDIs can provide excellent π-conjugation, increased electronic coupling, and limited aggregation effects.

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Section: ■ Resultssupporting

confidence: 65%

Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

et al. 2021

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“…The second system was able to check the method at higher temperatures from about T = 337 K to T = 357 K. The detailed data for these systems are available in the literature. (8)(9)(10) The results of measurements for these two systems are summarized in table 1. The phase diagram for (4-bromochlorobenzene + 1,4-dibromobenzene) determined by the static dilatometric method together with the literature data are listed in table 3 and reproduced in figure 3.…”

Section: Testing Measurementsmentioning

confidence: 99%

The static dilatometric method with ultrasonic liquid level detection to determine phase diagrams and (solid+ liquid) equilibrium in (hexadecane + octadecane)

Parczewska

2000

The Journal of Chemical Thermodynamics

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“…This apparatus has been tested before with measurements of densities for nonane and decane and their binary mixtures [11]. Additionally, to check the performance of the VTD the densities of the pure compounds were compared with literature values [12][13][14][15][16][17][18][19][20][21][22][23][24].…”

Section: Equipment and Proceduresmentioning

confidence: 99%

Densities and Excess Molar Volumes of Alkane (Heptane, Octane, Nonane, or Decane) + Thiophene from T=293.15 to 313.15 K

et al. 2012

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Densities of four binary systems composed of an alkane (heptane, octane, nonane, or decane) and thiophene were measured at temperatures from 293.15 to 313.15 K at atmospheric pressure (0.7 atm). Measurements were made covering the full range of compositions for all systems studied and for the pure compounds by using a vibrating-tube densimeter (VTD). Excess molar volumes have been obtained from these experimental results and were fitted to a Redlich-Kister type expansion. The excess molar volumes exhibit positive deviations from ideal behavior for all of the binary systems studied here.

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Physical Properties of Thiophene¹

Cited by 47 publications

References 0 publications

Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

The static dilatometric method with ultrasonic liquid level detection to determine phase diagrams and (solid+ liquid) equilibrium in (hexadecane + octadecane)

Densities and Excess Molar Volumes of Alkane (Heptane, Octane, Nonane, or Decane) + Thiophene from T=293.15 to 313.15 K

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Physical Properties of Thiophene1

Cited by 47 publications

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Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

Impact of Ring-Fusion on the Excited State Decay Pathways of N-Annulated Perylene Diimides

The static dilatometric method with ultrasonic liquid level detection to determine phase diagrams and (solid+ liquid) equilibrium in (hexadecane + octadecane)

Densities and Excess Molar Volumes of Alkane (Heptane, Octane, Nonane, or Decane) + Thiophene from T=293.15 to 313.15 K

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Physical Properties of Thiophene¹