Perylene-Fused BODIPY Dye with Near-IR Absorption/Emission and High Photostability

Abstract

A N-annulated perylene unit was successfully fused to the meso- and β-positions of a boron dipyrromethene (BODIPY) core. The newly synthesized BODIPY dye 1b exhibits intensified near-infrared (NIR) absorption and the longest emission maximum ever observed for all BODIPY derivatives. In addition, this dye possesses excellent solubility and photostability, beneficial to practical applications.

BODIPY‐Fused Porphyrins as Soluble and Stable Near‐IR Dyes

“…The design is based on the following considerations: 1) The BODIPY core provides a nice "zigzag" edge geometry for fusion of an aromatic unit (e.g., porphyrin) to the meso and b positions. Because perylene-fused BODIPY dyes exhibit absorption between 600 and 800 nm, as we have reported previously, [13] porphyrin-fused BODIPY dye is supposed to display enhanced NIR absorption, due to the larger conjugation in the latter.…”

“…[12] Fusing the BODIPY core to the other aromatic rings has rarely been reported. [13] In the past year we have been working on the synthesis of BODIPY-fused porphyrins, such as compounds 1 and 2 (Scheme 1). The design is based on the following considerations: 1) The BODIPY core provides a nice "zigzag" edge geometry for fusion of an aromatic unit (e.g., porphyrin) to the meso and b positions.…”

“…Our previous studies have pointed out that a fused BODIPY unit is the most effective building block, reported so far, for stabilization of the highly electron-rich, N-annulated perylene. [13] As a result, the porphyrin-fused BODIPY compound is expected to be a stable NIR dye in spite of its narrow band gap. 3) Generally speaking, the BODIPY core has relatively high reactivity and can undergo electrophilic substitution.…”

A Bodipy-Phenol-Based Sensor for Selectively Recognizing Three Basic Anions

“…of the fluorophore 27,28 . Both 1 and 2 displayed a strong emission band at about 590 nm with small Stokes shift.…”

Synthesis and Electroluminescent Properties of OLED Green Dopants Based on BODIPY Derivatives

“…2,[5][6][7][8] The development of new BODIPY derivatives has become a booming of research due to their potential applications in luminescent devices, chemical sensors, biological labeling, and photovoltaic cells. [9][10][11][12] Major efforts have been devoted to obtain the welldesigned BODIPY structures by modifying of the pyrrole core, fusing some aromatic rings to the BODIPY core, and replacing the 8-carbon atom with a nitrogen atom to form aza-BODIPY. The incorporation of boron element into the π-conjugated framework may lead to the appearance of unique electronic and photophysical properties.…”