D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

Wang, Chuan‐Zeng; Do, Jung‐Hee; Akther, Thamina; Feng, Xing; Horsburgh, Lynne; Elsegood, Mark R. J.; Redshaw, Carl; Yamato, Takehiko

doi:10.1016/j.tet.2016.11.077

Cited by 11 publications

(9 citation statements)

References 52 publications

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“…The observed lower dynamic kSV for singlet quenching (Figure S33) could be explained by the insignificant fluorescence quantum yield value of IEF-5. In fact, a low value of fluorescence quantum yield has been reported for the DTT monomer (F = 0.01), 72 being probably much lower for IEF-5 in accordance with the results obtained through fluorescence measurements (Figure 4A). Thus, it can be assured that charge transfer from the electron donor occurs via excited triplet state.…”

Section: Core Hole Clock (Chc) Synchrotron Experiments Allow Meas-supporting

confidence: 89%

Fundamental Insights into Photoelectrocatalytic Hydrogen Production with a Hole-Transport Bismuth Metal–Organic Framework

et al. 2019

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Solar fuels production is a cornerstone in the development of emerging sustainable energy conversion and storage technologies. Light-induced H 2 production from water represents one of the most crucial challenges to produce renewable fuel. Metalorganic frameworks (MOFs) are being investigated in this process, due to the ability to assemble new structures with the use of suitable photoactive building blocks. However, the identification of the reaction intermediates remains elusive, having negative impacts in the design of more efficient materials. Here, we report the synthesis and characterization of a new MOF prepared with the use of bismuth and dithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acid (DTTDC), an electron-rich linker with hole transport ability. By combining theoretical studies and time-resolved spectroscopies, such as core hole clock and laser flash photolysis measurements, we have completed a comprehensive study at different time scales (fs to-ms) to determine the effect of competitive reactions on the overall H 2 production. We detect the formation of an intermediate radical anion upon reaction of photogenerated holes with an electron donor, which plays a key role in the photoelectrocatalytic processes. These results shed new light on the use of MOFs for solar fuel production.

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Section: Core Hole Clock (Chc) Synchrotron Experiments Allow Meas-supporting

confidence: 89%

Fundamental Insights into Photoelectrocatalytic Hydrogen Production with a Hole-Transport Bismuth Metal–Organic Framework

et al. 2019

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“…The closely separated HOMOs and LUMOs resulted from the presence of the strong electron-donating nature of the N,N-diphenylaminophenyl groups. In this process, the ICT plays an important role in lowering the energy gap (ΔE), 19 which is consistent with the excitation spectra.…”

Section: Photophysical Propertiessupporting

confidence: 76%

Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene

Wang

Hee

Akther

et al. 2017

Journal of Luminescence

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We herein present four highly fluorescent and stable D-π-D monomers (2), which were designed and synthesized using different types of aryl substituent as the donor via a Suzuki-Miyaura coupling reaction. We have studied these four symmetrical chromophores by UV-vis absorption and fluorescence emission spectroscopy both in solution and the solid state. This research shows that the introduction of the aryl groups can effectively extend the conjugation length of thiophene chromophore resulting in a shift of the wavelength of the absorption and fluorescence emission and an improvement of the fluorescence quantum yields. The notable optical features of their solid-state powders also exhibited a distinct red-shift in comparison with the emissions of their dilute solutions. These results combined with the theoretical calculations (B3LYP/6-31G*) indicate that these systems are promising candidates in the fabrication of organic electroluminescence devices.

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“…Direct introduction of an aromatic ethynyl group to a polycyclic core can extend the conjugation of the π-system to a great extent, leading to significant modification of the properties of the original materials. Two known OLED materials, namely, a D-A-D chromophore based on 2,1,3benzothiadiazole (3q) 21 and a D-π-D chromophore based on dithieno[3,2-b:2′,3′-d]thiophene (3r), 22 were successfully synthesized using our method. The moderate to high yields (99% and 65%) indicate the high reactivity of phenylacetylene (1b).…”

Section: Resultsmentioning

confidence: 99%

Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems

et al. 2022

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D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

Cited by 11 publications

References 52 publications

Fundamental Insights into Photoelectrocatalytic Hydrogen Production with a Hole-Transport Bismuth Metal–Organic Framework

Fundamental Insights into Photoelectrocatalytic Hydrogen Production with a Hole-Transport Bismuth Metal–Organic Framework

Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene

Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems

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