20033-74-3Relevant academic research and scientific papers
Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: Effects of the substitution positions of the amino functionality on the photophysical properties
Wang, Lei,Fujii, Mayu,Yamaji, Minoru,Okamoto, Hideki
, p. 1319 - 1328 (2018)
The absorption and fluorescence spectra of a series of 1,8-naphthalimide derivatives incorporating the amino functionality at the 2-, 3- and 4-positions of the naphthalene ring (2APNI, 3APNI and 4APNI, respectively) were systematically investigated in various solvents and in the solid state. The fluorescence spectra of 2APNI were insensitive to solvent polarity and intermolecular hydrogen-bonding even in a protic medium such as methanol. Thus, 2APNI displayed blue fluorescence with a moderate fluorescence quantum yield (λFmax = 420-445 nm, ΦF 0.2-0.3) in the solvents investigated. In contrast, the fluorescence spectra of 3APNI and 4APNI were strongly solvent dependent showing positive solvatofluorochromism with large Stokes shifts. Upon increasing the solvent polarity, the fluorescence colours changed from blue in hexane (λFmax = 429 nm) to orange-yellow in methanol (λFmax = 564 nm) for 3APNI, and from blue in hexane (λFmax = 460 nm) to yellow in methanol (λFmax = 538 nm) for 4APNI. The fluorescence quantum yields of 3APNI and 4APNI decreased with increasing solvent polarity. In the solid state, APNIs displayed red-shifted fluorescence emission compared to that in solution (λFmax = 541 nm for 2APNI, 575 nm for 3APNI, and 561 nm for 4APNI) and the fluorescence quantum yields in the solid state were lower than those in solution.
Investigations into the reactivity of lithium indenyl with alpha diimines with chlorinated backbones and formation of related functional ligands and metal complexes
Chen, Chi-Tien,Fischer, Mark E.,Windsor, Caroline,Vei, Ino C.,Calatayud, David G.,Green, Malcolm L.H.,Pascu, Sofia I.
, p. 532 - 547 (2016)
Reaction between lithium indenyl and a chlorine substituted alpha diimine of the form [{Cl(NPh)2}C)]2unexpectedly yielded the corresponding NH rearranged derivative [PhN(H)C(C9H6)]2(1) rather than the
Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives
Gendron, David,Gann, Eliot,Pattison, Katherine,Maasoumi, Fatemeh,McNeill, Christopher R.,Watkins, Scott E.,Burn, Paul L.,Powell, Benjamin J.,Shaw, Paul E.
, p. 4276 - 4288 (2014/06/09)
The synthesis of three pyrrolo[3,2-b]pyrrole-1,4-dione (isoDPP) derivatives is described, namely 1,3,4,6-tetraphenylpyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione 2, 1,4-diphenyl-3,6-di(thiophen-2-yl)pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione 3, and 1,4-bis(4-(hexylo
Pyrrolo[3,2-b]pyrrole-based copolymers as donor materials for organic photovoltaics
Song, Suhee,Ko, Seo-Jin,Shin, Hyunmin,Jin, Youngeup,Kim, Il,Kim, Jin Young,Suh, Hongsuk
, p. 3399 - 3404 (2014/01/06)
A new accepter unit, pyrrolo[3,2-b]pyrrole-2,5-dione, was prepared and utilized for the synthesis of the conjugated polymers containing electron donor-acceptor pair for OPVs. Pyrrolo[3,2-b]pyrrole-2,5-dione unit, regioisomer of the known pyrrolo[3,4-c]pyrrole-1,4-dione, is originated from the structure of stable synthetic pigment. The new conjugated polymers with 1,4-diphenylpyrrolo[3,2-b]pyrrole-2,5-dione, thiophene and carbazole were synthesized using Suzuki polymerization to generate P1 and P2. The solid films of P1 and P2 show absorption bands with maximum peaks at about 377, 554 and 374, 542 nm and the absorption onsets at 670 and 674 nm, corresponding to band gaps of 1.85 and 1.84 eV, respectively. To improve the hole mobility of the polymer with 1,4-bis(4-butylphenyl)-pyrrolo[3,2-b]-pyrrole-2,5-dione unit, which was previously reported by us, the butyl group at the 4-positions of the N-substituted phenyl group was substituted with hydrogen and methyl group. The field-effect hole mobility of P2 is 9.6 × 10-5 cm2/Vs. The device with P2:PC71BM (1:2) showed VOC value of 0.84 V, JSC value of 5.10 mA/cm2, and FF of 0.33, giving PCE of 1.42%.
Synthesis and structural investigations of Ni(II)- and Pd(II)-coordinated α-diimines with chlorinated backbones
Pascu, Sofia I.,Balazs, Gabor,Green, Jennifer C.,Green, Malcolm L.H.,Vei, Ino C.,Warren, John E.,Windsor, Caroline
body text, p. 1157 - 1172 (2010/06/18)
Novel square planar Pd(II) α-diimines [PdX2{ArN{double bond, long}C(Cl)}2], where Ar = C6H5, (2,6-Me2C6H3), (2,6-iPr2C6H3) and X = Cl or Br, and the octahedral Ni(II) complex [NiBr2{(C6H5)N{double bond, long}C(Cl)}2(THF)2] have been prepared and characterised by spectroscopic methods. For two of the Pd(II) complexes and the Ni(II) complex the crystal structures were determined by X-ray crystallography. A further insight into the geometry and electronic structure of [PdBr2{(2,6-Me2C6H3)N{double bond, long}C(Cl)}2] was gained using density functional theoretical calculations (DFT). This compound resembles structurally and electronically typical olefin polymerisation pre-catalysts supported by α-diimines incorporating methyl- and 1,8-naphtalenyl substituents at the ligand backbone. The chlorine-substituted backbone of the free ligand [2,6-Me2C6H3N{double bond, long}C(Cl)]2 can be employed in further alkylation reactions to generate new multifunctional ligand prototypes with potential uses as ansa-metallocene/diimines building blocks for catalytic applications of heterobimetallic complexes.
A new route to ring-fused pyrazines: Imidazo[4,5-b]quinoxalines by a simple oxidation-annulation sequence
Herzoge, Svenja,Buehrdel, Gunther,Beckert, Rainer,Klimas, Susann,Wuerthwein, Ernst-Ulrich,Grimme, Stefan,Goerls, Helmar
experimental part, p. 4049 - 4057 (2010/03/24)
Novel tricyclic 4H-imidazo[4,5-b]quinoxalines were synthesized by a new orfto-annulation process starting from 4Himidazoles and cerammonium nitrate (CAN) as oxidation reagent in the presence of potassium carbonate as base. This reaction is interpreted as
A new synthesis of bis-enaminones via acylation of ketones
Buehrdel, Gunther,Beckert, Rainer,Petrlikova, Eva,Herzigova, Petra,Klimesova, Vera,Fleischhauer, Jan,Goerls, Helmar
experimental part, p. 3071 - 3080 (2009/04/06)
A short and efficient synthesis for a series of 1,6-diaryl-3,4- diarylaminohexa-2,4-diene-1,6-diones was developed. Based on the acylation-prototropism sequence during the reaction of various aryl methyl ketones with bis-imidoyl chlorides, the products were isolated in good yields. Substituted acetophenones, acetylthiophene, 3-acetylpyridine, and acetylferrocene can be integrated into this reaction as ketone component. Similarly, α-tetralone can be transformed with bis-electrophiles into the corresponding bis-enaminones. Treatment of 2-acetylpyridine with N,N′-bis(4-tolyl)ethanebis(imidoyl) dichloride yielded not only the expected bis-enaminone, but also a new quinolizine derivative which was structurally characterized by single crystal X-ray analysis. Analogously, pinacolone and cyclopropyl methyl ketone can readily be converted into bis-enaminones. Monoimidoyl chlorides showed the same reactivity, providing derivatives in high yields. Georg Thieme Verlag Stuttgart.
Tetrazoles: XL. Structure and basicity of 1,1′-disubstituted 5,5′-bitetrazoles
Ostrovskii,Kochkina,Shcherbinin,Koldobskii
, p. 1824 - 1830 (2007/10/03)
1,1′-Diaryl-5,5′-bitetrazoles, unlike 1,1′-dimethyl derivative, are Hammett bases which are much weaker than their monocyclic analogs. Bitetrazoles undergo monoprotonation in the H0 range from -5 to -9, and their pKBH+ values correla
Preparation of 1,5-disubstituted tetrazoles under phase-transfer conditions
Artamonova,Zhivich,Dubinskii,Koldobskii
, p. 1428 - 1430 (2007/10/03)
Imidoyl chlorides, obtained by common methods from a wide range of aromatic mono- and diamides, are smoothly converted to the corresponding tetrazoles in high yields by treatment with NaN3 under phase-transfer conditions.
