Synthesis of a new type of dibenzopyrromethene–boron complex with near-infrared absorption property

BODIPY‐Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin‐Film Transistors

“…[65] These molecules absorb near-infrared light with relatively high molecular extinction coefficients. Prior to this study, the group has developed new types of BODIPYs with benzo [1,3,2] oxazaborinine π-core relying on intramolecular BÀ O chelation, [84] which led to a red shift in the absorption band [85,86] yielding near-infrared absorbing dyes. Through comparison with the corresponding hexyloxy derivative, the effect of thiophene insertion on the absorption property was examined.…”

New Trends in Near-Infrared Fluorophores for Bioimaging

“…58 Much work has been published on the basis of this concept over the past years (e.g. benzo-fused BODIPY (112 -164), [59][60][61][62][63][64] benzo-fused B,O-chelated BODIPY (165 -167), 65,66 benzo-fused aza-BODIPY (168 -177), 37,67,68 and areno-fused BODIPY (178 -186) 69,70 ), and the following briefly describes the tendency of the effect of modifying the optical properties: about a 50 nm red shift is achieved by introducing one benzene ring, resulting in similar, or a bit lower, optical properties compared to that of the original BODIPY (spectral sharpness, extinction coefficients, quantum yields). The extinction coefficients are for the most part almost identical to, or lower than, those of BODIPY (~80000 M -1 cm -1…”

A Solution‐Processable meso‐Phenyl‐BODIPY‐Based n‐Channel Semiconductor with Enhanced Fluorescence Emission

“…In the past few decades, BODIPY‐based small molecules have been studied as fluorescent switches/sensors, chemosensors, biochemical labels, and photodynamic therapy agents, and they have shown remarkable photophysical properties such as high fluorescence quantum yield, large extinction coefficient, small Stokes shifts, high photostability, and tunable absorption/fluorescence profiles . The recent optoelectronic applications of BODIPY π‐systems include organic photovoltaics (OPVs), dye‐sensitized solar cells (DSSCs), organic field‐effect transistors (OFETs), light harvesting, and near‐infrared absorption . Owing to its highly π‐electron deficient electronic structure resulting in an energetically stabilized frontier orbitals, BODIPY is one of the unique π‐acceptor building blocks that could be synthesized and functionalized in a few steps.…”

“…[19] The recent optoelectronic applications of BODIPY πsystems include organic photovoltaics (OPVs), [20] dye-sensitized solar cells (DSSCs), [21] organic field-effect transistors (OFETs), [22] light harvesting, [23] and near-infrared absorption. [24] Owing to its highly π-electron deficient electronic structure resulting in an energetically stabilized frontier orbitals, BODIPY is one of the unique π-acceptor building blocks that could be synthesized and functionalized in a few steps. Thanks to its excellent structural properties including high π-core planarity, large dipole moment (μ~3-4 D), good π-delocalization, and high solubility, BODIPY is an ideal building block to form solutionprocessable donor-acceptor (D-A) type n-channel semiconductor architectures.…”