Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

• Kosuke Takemura,
• Kazuki Ohira,
• Taiki Higashino,
• Keiichi Imato and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

• stannyl D–π unit with 1,3-diiodobenzene, respectively. Their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, time-resolved fluorescence spectroscopy, cyclic voltammetry (CV) and molecular orbital (MO) calculations. In toluene the photoabsorption

• properties (Φfl-solid = 0.24 nm), compared with OTK-2 (Φfl-solid = 0.15 nm). CV results demonstrated that OTT-2 and OTK-2 exhibit a reversible oxidation wave. Based on photoabsorption, fluorescence spectroscopy and CV for the two dyes, it was found that the lowest unoccupied molecular orbital (LUMO) energy

• level of OTT-2 is lower than that of OTK-2, but OTT-2 and OTK-2 have comparable highest occupied molecular orbital (HOMO) energy levels. Consequently, this work reveals that compared to the (D–π)2Ph-type structure, the (D–π)2-type structure exhibits not only a bathochromic shift of the photoabsorption

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• properties of the three dyes were investigated by photoabsorption and fluorescence spectroscopy, Lippert–Mataga plots, cyclic voltammetry and density functional theory calculations. The photoabsorption maximum (λmax,abs) and the fluorescence maximum (λmax,fl) for the intramolecular charge-transfer

• characteristic band of the (D–π–)2A fluorescent dyes show bathochromic shifts in the order of OUY-2 < OUK-2 < OUJ-2. Moreover, the photoabsorption bands of the (D–π–)2A fluorescent dyes are nearly independent of solvent polarity, while the fluorescence bands showed bathochromic shifts with increasing solvent

• . Thus, the D–π–A dyes exhibit intense photoabsorption and fluorescence emission properties based on the intramolecular charge transfer (ICT) excitation from the D moiety to the A moiety [1][2][3][4]. Moreover, the D–π–A structure possesses considerable structural characteristics: the increase in the

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• synthesized. Based on density functional theory calculations, the star-shaped TTA-DPP4 has a larger oscillator strength than the linear TTA-DPP2, and consequently, better photoabsorption property over a wide range of visible wavelengths. The photovoltaic properties of organic solar cells based on TTA-DPP4 and

• ability, and good miscibility with a fullerene derivative as an acceptor. Moreover, strong visible light photoabsorption ability for visible light is vital for the donor materials. Star-shaped molecules tethering multiple π-conjugated arms are capable of harvesting incident light effectively owing to

• -OSCs. The design of star-shaped π-conjugated molecules offers possibilities for not only further enhancement of the photoabsorption ability but also for the improvement of molecular packing, solubility, and film-forming ability. However, the impact of star-shaped molecular structures on optoelectronic