The nature of the excited states of p-nitro-N,N-dimethylaniline

Dobkowski, Jacek; Herbich, Jerzy; Waluk, Jacek; Koput, Jacek; Kühnle, W.

doi:10.1016/0022-2313(89)90050-1

Cited by 18 publications

(36 citation statements)

References 30 publications

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“…It is very clear from (16). This was predicted on the basis of a linear correlation of the TICT fluorescence maxima with the difference of the oxidation potential of the donor and the reduction potential of the acceptor group, which has been found for several molecules showing TICT fluorescence.…”

Section: Discussionmentioning

confidence: 73%

On the ground and excited state dipole moments of planar vs. twisted nitroaniline analogues

Sinha¹,

Yates²

1991

Can. J. Chem.

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. 69,550 (1991). Planar and conformationally twisted p-nitroaniline (PNA) and N,N-dimethyl-p-nitroaniline (DMPNA) systems have been subjected to electric field study (electrochromism) to understand their charge transfer characteristics in the ground and excited states. The observed values of ground and excited state dipole moments suggest that twisting of either the donor (D) with respect to the acceptor (A) or vice versa can have a large impact on the resultant charge distribution, particularly on the excited state charge distribution. These observations remarkably support the TICT hypothesis and minimum overlap rule, as proposed by Grabowski et al. Simple molecular orbital calculations provide adequate explanation for the observed changes in the dipole moment and reasonable agreement has been found in each case studied.

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Section: Discussionmentioning

confidence: 73%

On the ground and excited state dipole moments of planar vs. twisted nitroaniline analogues

Sinha¹,

Yates²

1991

Can. J. Chem.

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“…Studies of disubstituted benzenes 29 , bis-ethynobenzenes 30 , disubstituted naphthalenes 31 , and fused nitro-fluorenes 32,33 demonstrate these design principles for organic branched fluorescent nitro-aromatics. In these examples, an increase in solvent polarity increases the fluorescence efficiency, which indicates that radiative deactivation occurs from states with a pronounced CT character 8,34 .…”

mentioning

confidence: 87%

Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2-b]pyrroles

et al. 2020

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Electron-deficient π-conjugated functional dyes lie at the heart of organic optoelectronics. Adding nitro groups to aromatic compounds usually quenches their fluorescence via inter-system crossing (ISC) or internal conversion (IC). While strong electronic coupling of the nitro groups with the dyes ensures the benefits from these electron-withdrawing substituents, it also leads to fluorescence quenching. Here, we demonstrate how such electronic coupling affects the photophysics of acceptor–donor–acceptor fluorescent dyes, with nitrophenyl acceptors and a pyrrolo[3,2-b]pyrrole donor. The position of the nitro groups and the donor-acceptor distance strongly affect the fluorescence properties of the bis-nitrotetraphenylpyrrolopyrroles. Concurrently, increasing solvent polarity quenches the emission that recovers upon solidifying the media. Intramolecular charge transfer (CT) and molecular dynamics, therefore, govern the fluorescence of these nitro-aromatics. While balanced donor-acceptor coupling ensures fast radiative deactivation and slow ISC essential for large fluorescence quantum yields, vibronic borrowing accounts for medium dependent IC via back CT. These mechanistic paradigms set important design principles for molecular photonics and electronics.

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“…Its relative simplicity, however, has attracted some attention to it and its derivatives for studies aiming at deciphering the excited-state dynamics and fluorescence properties of nitroaromatics. 86,87 Enhancing the CT character of nitrobenzene by converting it to nitroaniline, actually, leads to some weak but detectable fluorescence. 87…”

Section: Suppressing Intersystem Crossing In Non-polar Solventsmentioning

confidence: 99%

“…86,87 Enhancing the CT character of nitrobenzene by converting it to nitroaniline, actually, leads to some weak but detectable fluorescence. 87…”

Section: Suppressing Intersystem Crossing In Non-polar Solventsmentioning

confidence: 99%

Revisiting the non-fluorescence of nitroaromatics: presumption versus reality

et al. 2022

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The nature of the excited states of p-nitro-N,N-dimethylaniline

Cited by 18 publications

References 30 publications

On the ground and excited state dipole moments of planar vs. twisted nitroaniline analogues

On the ground and excited state dipole moments of planar vs. twisted nitroaniline analogues

Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2-b]pyrroles

Revisiting the non-fluorescence of nitroaromatics: presumption versus reality

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