20033-74-3Relevant articles and documents
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.
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
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.
