765911-39-5Relevant academic research and scientific papers
Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
, p. 7081 - 7092 (2016/10/14)
We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.
Design and synthesis of the first triply twisted Moebius annulene
Schaller, Gaston R.,Topic, Filip,Rissanen, Kari,Okamoto, Yoshio,Shen, Jun,Herges, Rainer
, p. 608 - 613 (2014/07/08)
As long as 50 years ago theoretical calculations predicted that Moebius annulenes with only one π surface and one edge would exhibit peculiar electronic properties and violate the Hueckel rules. Numerous synthetic attempts notwithstanding, the first singly twisted Moebius annulene was not prepared until 2003. Here we present a general, rational strategy to synthesize triply or even more highly twisted cyclic π systems. We apply this strategy to the preparation of a triply twisted [24]dehydroannulene, the structure of which was confirmed by X-ray analysis. Our strategy is based on the topological transformation of 'twist' into 'writhe'. The advantage is twofold: the product exhibits a lower degree of strain and precursors can be designed that inherently include the writhe, which, after cyclization, ends up in the Moebius product. With our strategy, triply twisted systems are easier to prepare than their singly twisted counterparts.
Chiral binaphthalenes bearing two pyridine ligands attached via acetylene spacers. Synthesis and coordination study
Kasak, Peter,Brath, Henrich,Krascsenicsova-Polakova, Katarina,Kickova, Anna,Moldovan, Natalia,Putala, Martin
, p. 1139 - 1157 (2008/09/19)
An effective methodology has been developed for the synthesis of enantiopure 2,2′-dialkynylated 1,1′-binaphthalene derivatives. Enantiopure 2,2′-diiodo-1,1′-binaphthalene (10) provided 2,2′-diethynyl-1,1′-binaphthalene (16) in the Negishi alkynylation sup
Enantiopure double-helical alkynyl cyclophanes
An, De Lie,Nakano, Takehiko,Orita, Akihiro,Otera, Junzo
, p. 171 - 173 (2007/10/03)
The "commercially available chirality" of the binaphthyl units and the efficiency of the coupling reactions were crucial to the synthesis of double-helical alkynyl cylophanes 1 in enantiopure form. The unique properties of these molecules have been unambi
