2017
DOI: 10.1002/chem.201702306
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Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red‐Emitting Dyes with Conformational Freedom

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

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Cited by 16 publications
(21 citation statements)
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“…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
confidence: 85%
“…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
confidence: 85%
“…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.…”
Section: Design and Synthesismentioning
confidence: 99%
“…[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.…”
mentioning
confidence: 99%