81-30-1Relevant articles and documents
Electronic and assembly properties of a water-soluble blue naphthalene diimide
Draper, Emily R.,Matsarskaia, Olga,Schweins, Ralf,Welsh, Thomas A.
, p. 14005 - 14013 (2021)
Herein we report on the synthesis and characterisation of a water soluble deep blue naphthalene diimide, (iPrNH)2NDI-V. The synthesis is performed under mild conditions and careful consideration of the purification of the precuror materials leads to improved results in final yield and purity. The optoelectronic properties are explored through cyclic voltammetry and UV-vis absorption and emission spectroscopy in multiple solvents and the self-assembling properties as part of a multi-component hydrogel are investigated through rheology and small angle neutron scattering.
Conformationally rigid molecular and polymeric naphthalene-diimides containing C6H6N2constitutional isomers
Abbinante, Vincenzo Mirco,Barba, Luisa,Calabrese, Gabriele,García-Espejo, Gonzalo,Giannici, Francesco,Guagliardi, Antonietta,Marini, Diego,Masciocchi, Norberto,Milita, Silvia,Pipitone, Candida
, p. 10875 - 10888 (2021/09/02)
Organic thin films based on naphthalenediimides (NDIs) bearing alkyl substituents have shown interesting properties for application in OLEDs, thermoelectrics, solar cells, sensors and organic electronics. However, the polymorphic versatility attributed to the flexibility of alkyl chains remains a challenging issue, with detrimental implications on the performances. Aryl analogues containing C6H6N2 constitutional isomers are herein investigated as one of the possible way-out strategies. The synthesis of molecular and polymeric species is described, starting from naphthaleneteracarboxyldianhydride with isomeric aromatic amines and hydrazine. The materials are fully characterized by spectroscopy, thermal and structural X-ray diffraction methods, both as bulk powders and thin films, revealing a rich structural landscape. Depending on the stereochemistry of the branching aryls, the compounds show a variety of parallel stacking of the NDI cores, and high structural stability upon heating, up to 560 °C in the polymeric form. Thin films prepared by spin coating from organic solvent solutions and studied by grazing-incidence X-ray diffraction exhibit a high degree of crystallinity indicating the intrinsic tendency of these molecules to self-assemble in an ordered fashion without the need for any post-processing technique. In line with other NDI-based diimides, UV-vis spectroscopy indicates the optical band gaps falling in the visible region (2.87-3.02 eV). DFT calculations reveal a significant lowering of the frontier orbital energies of the hydrazido derivative. Beyond solution processing, the high thermal stability and the absence of polymorphic forms of these materials suggest that sublimation-based routes for films and device preparation can also be followed. This journal is
Mechanism of 1,4,5,8-naphthalene tetracarboxylic acid dianhydride hydrolysis and formation in aqueous solution
Barros,Cuccovia,Farah,Masini,Chaimovich,Politi
, p. 71 - 82 (2007/10/03)
The study of highly conjugated, carbonyl-containing molecules such as 1,4,5,8-naphthalene tetracarboxylic dianhydride, III, is of interest since reactivity differences and transmission of electronic effects through the conjugated framework can be evidenced. The kinetics of hydrolysis of III in aqueous solution were determined from 5 M acid to pH 10. In basic solution hydrolysis of III yields, sequentially, 1,4,5,8-naphthalene diacid monoanhydride, II, and 1,4,5,8-naphthalene tetracarboxylic acid, I. The second order rate constant for alkaline hydrolysis is 200 fold higher for the first ring opening. The water-catalyzed hydrolysis of III yields a pH-dependent mixture of ionic forms of I and II. The rate constant for water-catalyzed hydrolysis of III is 25 fold higher than that for II. In concentrated acid the rates for reaching equilibrium (I, II and III) increase and III is the major product. The pKas of I (3.24, 5.13 and 6.25) and II (3.05, 5.90) were determined by potentiometric, fluorescence and UV spectroscopy titrations and by quantitative fit of the kinetic and equilibrium data. The apparent, pH-dependent, equilibrium constants, KEqII, for anhydride formation between I and II were obtained from the UV spectra. The quantitative fit of kinetic and equilibrium data are consistent with the assumption that anhydride formation only proceeds with the fully protonated species for both I and II and permitted the estimation of the equilibrium constants for anhydride formation, KEqII. The value of KEqII (I II) between pH 1 and 6 was ca. 5. Geometry optimization calculations in the gas phase of the reactions of III in alkaline, neutral and acid conditions, at the DFT level of theory, gave electronic distributions that were qualitatively consistent with the experimental results. The Royal Society of Chemistry 2006.
