Asymmetrical benzo[a]-fused N₂O₂-boron-chelated BODIPYs as red to near-infrared absorbing chromophores: synthesis, characteristics and device applications for opto-electronics

Abstract

Asymmetric benzo[a]-fused BODIPYs with benzo(thieno)[1,3,2]oxazaborinine units 1–4 were synthesized, not only the relationship between the structure and photophysical properties but also a potential device application being investigated.

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

“…IR spectra were recorded on a SHIMADZU IRTracer-100 spectrometer by ATR method. 1 H NMR and 13 C NMR spectra were recorded on a Varian-500 FT NMR spectrometer. Highresolution mass spectral data by APCI were acquired on a Thermo Fisher Scientific LTQ Orbitrap XL apparatus.…”

“…The design and development of a new type of organic fluorescent dyes have been of considerable scientific and practical concern with the objective of not only fundamental studies [1][2][3][4][5][6][7][8][9][10][11][12][13] in synthetic chemistry, electrochemistry and photochemistry, but also their potential applications to emitters for optoelectronic devices, such as organic light-emitting diodes (OLEDs) [14][15][16][17][18][19][20][21][22], as well as fluorescent probes [23][24][25][26][27][28] for bioimaging and fluorescent sensors for specific target species [29][30][31][32]. Among many kinds of organic fluorescent dyes, much efforts have been made on the development of donor-π-acceptor (D-π-A)-type fluorescent dyes constructed of an electron-donating moiety (D) and an electron-withdrawing moiety (A), linked by a π-conjugated unit thanks to their intense photoabsorption and fluorescence emission characteristics originating from the intramolecular charge transfer (ICT) excitation from the D to the A moiety [4][5][6][7][8][9][18][19][20]25,…”

Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-<i>c</i>]carbazoloquinol Fluorescent Dyes

“…[1][2][3][4][5] In general, conventional fluorophores such as perylene, xanthene, cyanine, coumarin, and BODIPY skeletons have been modified by introducing various substituents or fusing aromatic ring to function as the desired sensors, probes or emitters for precision applications. [6][7][8][9][10] On the other hand, the development of new type of fluorophores can create new applications, as well as leading to dramatic improvement in fluorescence sensing and imaging and device performances. Thus, for this purpose, we have developed benzofuro [2,3-c]carbazoloquinone BfCzQ-1 as a useful intermediate which allows us to create various kinds of fluorophores (Fig.…”

Far-red fluorescence and chiroptical properties of pyrrolopyrrole aza-BODIPYs induced by the B,O-chelation

“…To achieve the redshift without sacrificing the high fluorescence quantum yields of PPABs, fixing phenyl substituents in a small dihedral angle by forming B,O-chelated structures was attempted in this study. The B,O-chelation [14][15][16][17][18] not only caused the redshifts of absorption and fluorescence but also provided two diastereomers (anti and syn isomers) relative to the direction of the substituents on the boron atom. Among them, the syn isomer was a chiral molecule.…”