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4-Dimethylamino-4′-nitrostilbene (CAS 2844-15-7)

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Alternate Names:
N,N-Dimethyl-4′-nitro-4-stilbenamine; DANS
Application:
4-Dimethylamino-4′-nitrostilbene is a useful standard for the correction of emission of fluorescence spectrometers
CAS Number:
2844-15-7
Molecular Weight:
268.31
Molecular Formula:
C16H16N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Dimethylamino-4′-nitrostilbene is a compound of interest in various research disciplines including materials science and organic chemistry. It is often used as a molecular probe to study the electronic effects of substituents on conjugated systems due to its electron-donating and electron-withdrawing groups at opposite ends of the molecule. This stilbene derivative is also a key subject in photophysics for its potential use in the design of organic dyes and fluorescent markers, where its strong absorption and emission properties are analyzed. In the realm of synthetic organic chemistry, researchers explore the reactivity of 4-Dimethylamino-4′-nitrostilbene in various chemical reactions, such as its participation in cycloadditions or its use as a precursor for synthesizing more complex aromatic compounds. Moreover, it is utilized in the study of charge transfer complexes, which are relevant for understanding the molecular basis of electronic conductivity in organic materials.


4-Dimethylamino-4′-nitrostilbene (CAS 2844-15-7) References

  1. Solvent effects on resonant first hyperpolarizabilities and Raman and hyper-Raman spectra of DANS and a water-soluble analog.  |  Shoute, LC., et al. 2006. J Chem Phys. 125: 054506. PMID: 16942225
  2. Theoretical investigation on the effect of protonation on the absorption and emission spectra of two amine-group-bearing, red 'push-pull' emitters, 4-dimethylamino-4'-nitrostilbene and 4-(dicyanomethylene)-2-methyl-6-p-(dimethylamino) styryl-4H-pyran, by DFT and TDDFT calculations.  |  Petsalakis, ID., et al. 2010. J Phys Chem A. 114: 5580-7. PMID: 20384332
  3. Spectroscopic and DFT investigation on the photo-chemical properties of a push-pull chromophore: 4-Dimethylamino-4'-nitrostilbene.  |  Muniz-Miranda, F., et al. 2018. Spectrochim Acta A Mol Biomol Spectrosc. 190: 33-39. PMID: 28892719
  4. Fluorescent Paper Strips for the Detection of Diesel Adulteration with Smartphone Read-out.  |  Bell, J., et al. 2018. J Vis Exp.. PMID: 30474640
  5. Identification of microplastics using 4-dimethylamino-4'-nitrostilbene solvatochromic fluorescence.  |  Sancataldo, G., et al. 2021. Microsc Res Tech. 84: 2820-2831. PMID: 34047435
  6. Twisted intramolecular charge transfer of nitroaromatic push-pull chromophores.  |  Lee, S., et al. 2022. Sci Rep. 12: 6557. PMID: 35449231
  7. Key trade‐offs for second harmonic generation in poled polymers  |  , et al. (1996). Appl. Phys. Lett. 69,: 1991–1993.
  8. Influence of the solvent matrix on the overlapping of the absorption and emission bands of solute fluorescent dyes  |  , et al. (1980). Applied physics v. olume 23,: pages 369–372.
  9. Electric Poling of 4-(Dimethylamino)-4'-nitrostilbene in Poly(methyl methacrylate) Studied by Polarized Absorption Spectroscopy  |  Xuan Cao and Jeanne L. McHale. 1997. J. Phys. Chem. B., 101, 44,: 8843–8849.
  10. Photophysics of 4-dimethylamino-4′-cyanostilbene and 4-azetidinyl-4′-cyanostilbene. Time-resolved fluorescence and trans-cis photoisomerisation  |  YV Il'ichev, W Kühnle, KA Zachariasse - Chemical physics, 1996 - Elsevier. 1 November 1996,. Chemical Physics. Volume 211, Issues 1–3,: Pages 441-453.
  11. Spectroelectrochemical studies of the adsorption of 4-dimethylamino-4′-nitrostilbene on silver and gold electrodes  |  R Holze - Vibrational spectroscopy, 1992 - Elsevier. 7 July 1992,. Vibrational Spectroscopy. Volume 3, Issue 4,: Pages 255-263.
  12. Dipole moment changes in the singlet and triplet excited states of 4-dimethylamino-4′-nitrostilbene detected by nanosecond time-resolved microwave conductivity  |  JM Warman, MP De Haas, A Hummel… - Chemical Physics …, 1982 - Elsevier. 12 March 1982,. Chemical Physics Letters. Volume 87, Issue 1,: Pages 83-86.
  13. SERS and DFT investigation on push-pull molecules: 4-Dimethylamino- 4'-nitrostilbene adsorbed on silver colloidal nanoparticles  |   and Prof. Maurizio Muniz-Miranda, Dr. Francesco Muniz-Miranda, Prof. Alfonso Pedone. August 14, 2018. ChemistrySelect. Volume3, Issue30: Pages 8698-8702.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Dimethylamino-4′-nitrostilbene, 500 mg

sc-214235
500 mg
$124.00