Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers

Çakal, Deniz; Cihaner, Atilla; Önal, Ahmet M.

doi:10.1016/j.jelechem.2020.114000

Cited by 16 publications

(10 citation statements)

References 48 publications

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“…All dyes have two prominent absorption maxima in the visible range. The maximum in the short wavelength range (300–400 nm) corresponds to π–π* transitions of the conjugate system [ 31 , 32 , 33 ]. The intramolecular charge transfer (ICT) between the donor and acceptor parts of molecules is confirmed by the presence of a long-wave absorption maximum at 400–500 nm.…”

Section: Resultsmentioning

confidence: 99%

Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them

et al. 2021

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This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoВТD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials.

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Section: Resultsmentioning

confidence: 99%

Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them

et al. 2021

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“…To further confirm this hypothesis, Fourier transformed infrared (FT-IR) is studied. As shown in Figure 4d, FT-IR peaks of symmetric and asymmetric CO stretching at 1718 and 1689 cm −1 in Octyl-TPD [78] are shifted to lower wavenumber of 1712 and 1687 cm −1 upon mixing Octyl-TPD with LiTFSI (1:1 molar ratio), which indicates that the bond strength of CO is weakened due to interaction with Li ion. Consequently, the aromatic CC stretching (1515 cm −1 ) is shifted to a higher wavenumber (1523 cm −1 ) due to the interaction of the carbonyl group with the Li + ion.…”

Section: % and This Champion Pce Is Even Higher Than That Of The Amentioning

confidence: 90%

Capturing Mobile Lithium Ions in a Molecular Hole Transporter Enhances the Thermal Stability of Perovskite Solar Cells

Kim

Monfreid

et al. 2021

Advanced Materials

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A thermally stable perovskite solar cell (PSC) based on a new molecular hole transporter (MHT) of 1,3‐bis(5‐(4‐(bis(4‐methoxyphenyl) amino)phenyl)thieno[3,2‐b]thiophen‐2‐yl)‐5‐octyl‐4H‐thieno[3,4‐c]pyrrole‐4,6(5H)‐dione (coded HL38) is reported. Hole mobility of 1.36 × 10−3 cm2 V−1 s−1 and glass transition temperature of 92.2 °C are determined for the HL38 doped with lithium bis(trifluoromethanesulfonyl)imide and 4‐tert‐butylpyridine as additives. Interface engineering with 2‐(2‐aminoethyl)thiophene hydroiodide (2‐TEAI) between the perovskite and the HL38 improves the power conversion efficiency (PCE) from 19.60% (untreated) to 21.98%, and this champion PCE is even higher than that of the additive‐containing 2,2′,7,7′‐tetrakis(N,N‐di‐p‐methoxyphenylamine)‐9,9′‐spirobifluorene (spiro‐MeOTAD)‐based device (21.15%). Thermal stability testing at 85 °C for over 1000 h shows that the HL38‐based PSC retains 85.9% of the initial PCE, while the spiro‐MeOTAD‐based PSC degrades unrecoverably from 21.1% to 5.8%. Time‐of‐flight secondary‐ion mass spectrometry studies combined with Fourier transform infrared spectroscopy reveal that HL38 shows lower lithium ion diffusivity than spiro‐MeOTAD due to a strong complexation of the Li+ with HL38, which is responsible for the higher degree of thermal stability. This work delivers an important message that capturing mobile Li+ in a hole‐transporting layer is critical in designing novel MHTs for improving the thermal stability of PSCs. In addition, it also highlights the impact of interface design on non‐conventional MHTs.

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“…QY values were found to be 0.58, 0.57, and 0.44, for F 2 BT-F, T 2 BT-F, and S 2 BT-F, respectively. Monomer S 2 BT-F exhibited relatively lower QY compared to the other two monomers due to the quenching effect of heavier selenium atom [11,34,35]. In order to understand the effect of fluorine atom on QY, we have also measured the QYs of nonfluorinated and fully fluorinated analogues of T 2 BT-F, namely 4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (T 2 BT) and 5,6-difluoro-4,7-di(thiophen-2-yl)benzo [c][1,2,5]thiadiazole (T 2 BT-2F), respectively, which were synthesized in our previous works [27].…”

Section: Electrochemical and Optical Properties Of Monomersmentioning

confidence: 99%

Effect of the donor units on the properties of fluorinated acceptor based systems

et al. 2021

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A new series of monomers in the donor-acceptor-donor array, namely 5-fluoro-4,7-di(furan-2-yl)benzo [c][1,2,5] thiadiazole (F 2 BT-F), and 5-fluoro-4,7-di(selenophen-2-yl)benzo [c][1,2,5] thiadiazole (S 2 BT-F), bearing 5-fluorobenzo[c][1,2,5]-thiadiazole as the acceptor moiety and furan and selenophene as the electron donating groups was synthesized and polymerized electrochemically. To compare heteroatom effect, thiophene analogue of newly synthesized F 2 BT-F and S 2 BT-F namely, (5-fluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5] thiadiazole (T 2 BT-F)) and its corresponding polymer were also synthesized. Effect of donor units on the electrochemical and optical properties of fluorinated acceptor based systems was investigated in terms of the effect of different sized heteroatoms in five-membered rings on the dihedral angle and planarity. Theoretical calculations also suggested a deviation from planarity upon fluorination. Moreover, electrochemically obtained polymers possess low bandgap values (1.62 eV-1.68 eV for PF 2 BT-F and PS 2 BT-F, respectively) and exhibited electrochromic properties with relatively low switching times.

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Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers

Cited by 16 publications

References 48 publications

Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them

Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them

Capturing Mobile Lithium Ions in a Molecular Hole Transporter Enhances the Thermal Stability of Perovskite Solar Cells

Effect of the donor units on the properties of fluorinated acceptor based systems

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