BODIPY-core 1,7-diphenyl-substituted derivatives for photovoltaics and OLED applications

Abstract

In the current study we demonstrate an application of four previously synthesized 1,7-diphenyl-substituted BODIPY species for inverted photovoltaic cells and for organic light-emitting devices (OLEDs). Depending on the type of substituents or annulation of the pyridone rings these dyes exhibit spectral properties in the full visible region up to the near-infrared wavelengths. All the studied compounds show very strong visible absorption that can be ascribed to the low lying LUMO levels making them electronically suitable as acceptors for many donor materials. The best fabricated inverted photovoltaic device based on the BODYPI-core derivatives demonstrates a power conversion efficiency equal to 1.36% which is close to previously published reports for related species. Two kinds of deep red OLEDs (doped and undoped) with narrow electroluminescence spectra (full width at half maximum up to 45 nm) have been fabricated. Maximum brightness of 3900 cd m À 2 and an external quantum efficiency by 2.3% were achieved for the best OLED structure.

Selectivec-MYCG4 DNA recognition based on a fluorescent light-up probe with disaggregation-induced emission characteristics

“…Generally, the fluorescence of BODIPY dyes in the solid state or solution at high concentrations is significantly suppressed due to the strong π–π stacking interactions between the rigid BODIPY planes. 35 However, the introduction of the hydrophilic aniline group in the BODIPY core is likely to cause the aggregation of probe MRY-3 in aqueous solutions. To prove our hypothesis and verify the existence of the aggregation phenomenon, the spectral properties of MRY-3 were further evaluated in DMSO–water mixtures with different fractions of water ( f w ).…”

Effects of Intermolecular Hydrogen Bonding and Solvation on Enol–Keto Tautomerism and Photophysics of Azomethine–BODIPY Dyads

“…4 For this reason, BODIPYs have been applied to many fields such as light-driven sensors in biological systems, 5,6 imaging agents in medical diagnosis, 7,8 and light harvesters in photovoltaics. 9,10 Given the extraordinary significance of BODIPYs in experiments, many researchers have made theoretical and computational efforts to reveal their extraordinary photophysical properties. The optical properties of the BODIPY parent molecule can be modulated through attaching specific functional groups interpreted by intramolecular charge transfer (ICT), photoinduced electron transfer (PET), excited-state proton transfer (ESPT), twisted intramolecular charge transfer (TICT), and so on.…”

“…Boron–dipyrromethene derivatives (BODIPYs) were synthesized for the first time in 1968 and subsequently became a research hotspot in the field of dye chemistry due to their superior photophysical properties, including intense fluorescence emission with narrow peaks, large molar absorption coefficients, and excellent stability in both solution and solid state. − Fluorescence quantum yields as well as absorption and emission wavelengths of BODIPYs can be regulated via extensive substitution variations . For this reason, BODIPYs have been applied to many fields such as light-driven sensors in biological systems, , imaging agents in medical diagnosis, , and light harvesters in photovoltaics. , …”

AZABODIPY aggregates as a promising electroluminescent material for sustainable NIR OLED applications

“…30 On the other hand, devices with reasonable efficiencies based on deep-red and NIR electroluminescence (EL) from BODIPY derivatives can be found in the literature. 31–35…”

“…30 On the other hand, devices with reasonable efficiencies based on deep-red and NIR electroluminescence (EL) from BODIPY derivatives can be found in the literature. [31][32][33][34][35] In the present work we propose the use in OLED of the asymmetric AZABODIPY which is substituted in 1 and 7 positions with phenyl rings and in 3 and 5 positions with thiophenic fragments (DTDPAB, see Scheme 1). The electron-rich thienyl moiety increases the delocalization (conjugation) with a consequent further shift of the absorption and emission towards low energies in the NIR zone.…”