Abstract:A series of bis-aryl dipyrrolonaphthyridinediones (DPNDs) with various substitution patterns have been designed and synthesized by direct arylation. This reaction occurs regioselectively at positions 3 and 9, which gives a straightforward entry to unique dyes that absorb in the red/far-red region and emit in the far-red/NIR region. The photophysical properties (absorption and fluorescence wavelength) can be controlled by altering the steric hindrance and electronic character of the peripheral aryl group. The f… Show more
“…29). 11 In line with our previous study, 120 the DPND core (dye 82 ) as a whole behaves as a weak electron acceptor, eventually preventing a significant shift of the electron density toward the nitro group and giving rise to strongly fluorescent nitroaromatics. Conjugates of the acceptor–‘acceptor’–acceptor ( 89–94 ) or acceptor–‘acceptor’ type ( 84–88 ) fluoresce mainly in non-polar solvents and also in relatively dipolar dichloromethane with quantum yields up to 0.76 (among dipolar molecules) and 0.95 (among quadrupolar molecules), while in polar CH 3 CN almost all derivatives are weakly fluorescent.…”
Section: Suppressing Intersystem Crossing In Non-polar Solventssupporting
Recent surge in the literature concerning fluorescent nitro-aromatics enables to gain in-depth insight into processes governing the fate of these molecules in the excited state. Literature analysis reveals three distinct...
“…29). 11 In line with our previous study, 120 the DPND core (dye 82 ) as a whole behaves as a weak electron acceptor, eventually preventing a significant shift of the electron density toward the nitro group and giving rise to strongly fluorescent nitroaromatics. Conjugates of the acceptor–‘acceptor’–acceptor ( 89–94 ) or acceptor–‘acceptor’ type ( 84–88 ) fluoresce mainly in non-polar solvents and also in relatively dipolar dichloromethane with quantum yields up to 0.76 (among dipolar molecules) and 0.95 (among quadrupolar molecules), while in polar CH 3 CN almost all derivatives are weakly fluorescent.…”
Section: Suppressing Intersystem Crossing In Non-polar Solventssupporting
Recent surge in the literature concerning fluorescent nitro-aromatics enables to gain in-depth insight into processes governing the fate of these molecules in the excited state. Literature analysis reveals three distinct...
“…2 ). Pd-catalyzed direct arylation 35 of DPND 1 with the corresponding aryl bromides allows us to obtain the D–A and A–D–A conjugates with nitro groups at ortho , meta , para and peri positions with respect to the core (see ESI † for synthetic details). This shift in the position of the nitro groups varies their electronic coupling with the DPND moiety.…”
Section: Resultsmentioning
confidence: 99%
“…DPNDs are a series of cross-conjugated heterocyclic chromophores with unique photophysical and electrochemical properties that allow them to act as week electron donors or weak electron acceptors, 30,[35][36][37] making them an excellent choice for designing the D-A and A-D-A conjugates for this study. Biaryllike linkages enable weak coupling between the nitro group(s) and the DPND core (Fig.…”
“…[9][10][11][12][13] The dipyrrolonaphthyridinedione (DPND) core 14 is a unique chromophore in that it is composed of cross-conjugated electronrich and electron-poor moieties (pyrrole rings and carbonyl groups, respectively). Recently, the DPND core has been successfully employed in the construction of dyes with red/NIR emission, 15,16 OFETs, 17 stable singlet fission (SF) materials 18 with a distinctive adaptive aromaticity (dual aromaticity) or fluorescent nitroaromatics. 19 Due to the presence of donor and acceptor moieties the DPND core is polarized.…”
This communication describes the photophysical behavior of three analogs of cyclophane bearing the dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in...
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