17135-74-9Relevant articles and documents
Facile Route to Quadruply Annulated Borepins
Schickedanz, Kai,Radtke, Julian,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias
, p. 2842 - 2851 (2017)
A two-step synthesis sequence furnishes quadruply annulated borepins in high yields. The first step involves a nucleophilic substitution reaction between aryl-BF3K salts (aryl = mesityl, phenyl) and lithiated bromonapthalene derivatives LiNaphBr,R (HNaphBr,R = 8-bromonaphthalene (a), 5-bromoacenaphthene (b), 5-bromoacenaphthylene (c)). In the second step, the resulting heteroleptic triarylboranes aryl-B(NaphBr,R)2 (3a-c) are subjected to an intramolecular Ni-mediated Yamamoto reaction to close the seven-membered rings and create the borepins 4a-c. Only in the case of 3b is the Yamamoto reaction accompanied by a C-H activation reaction furnishing the 7-hydro-7-borabenzo[de]anthracene derivative 5. The product ratio 4b/5 can be influenced by control of the local Ni(0) concentration. The borepins 4a-c are benchtop stable and highly soluble even in hexane. Compounds 4a-c undergo reversible one-electron reduction; 4c is also able to accept a second electron in a reversible manner and already at moderate potential values (E1/2 = ?1.49 V and ?1.84 V (vs FcH/FcH+)). 4a, 4b, and 5 show photoluminescence in the blue-green region of the spectrum, while 4c is nonfluorescent, which is likely attributable to an intramolecular charge-transfer transition.
A single-molecule excimer-emitting compound for highly efficient fluorescent organic light-emitting devices
Hu, Jian-Yong,Pu, Yong-Jin,Nakata, Go,Kawata, So,Sasabe, Hisahiro,Kido, Junji
, p. 8434 - 8436 (2012)
A pyrene-containing single-molecule excimer-emitting compound, 1,8-bis(pyren-2-yl)naphthalene (BPyN), was synthesized. With BPyN as a host emitter, C545T-based green OLEDs were fabricated, exhibiting high efficiencies of 22 lm W-1, 22 cd A-1 and 6.2% external quantum efficiency (EQE) at 100 cd m-2, and 19 lm W-1, 22 cd A-1 and 6.2% EQE at 1000 cd m-2.
Noncovalent Interactions between Stacked Arenes in 1,8-Bis-(1-naphthyl)-naphthalenes
Chiarucci, Michel,Mazzanti, Andrea,Righi, Paolo,Bencivenni, Giorgio,Mancinelli, Michele
supporting information, p. 2594 - 2603 (2021/04/05)
A number of 1,8-bis(1-naphthyl)-naphthalenes, bearing different substituents in the 1-naphthyl moieties have been prepared to investigate the noncovalent interactions between the stacked arenes. The best geometries were determined by means of DFT calculations, and experimentally checked by NMR and electronic circular dichroism (ECD). High temperature NMR spectroscopy allowed for the determination of the balance between dispersive and electrostatic contributions (ratio between two diastereomeric syn/anti isomers of compounds 1–6), while ECD analysis of the syn isomers of compounds 3–5 allowed for a deeper insight on the electrostatic contributions that drive the geometry between the interacting rings. The two rings preferentially adopt a parallel displaced geometry, whose interaction energy is strongly influenced by the electrostatic features of the two naphthyl rings, and that dispersive forces play a very minor role.
Synthesis of 1,2-disubstituted acenaphthylenes by palladium-catalyzed annulation reactions of dibromoarenes with internal alkynes
An, Wenbo,Li, Gaoqiang,Ma, Jun,Tian, Youping,Xu, Feng
supporting information, p. 1585 - 1590 (2014/07/08)
A simple and versatile route to 1,2-disubstituted acenaphthylenes has been developed. The method involves palladium-catalyzed annulation of 1,8-dibromonaphthalene or 5,6-dibromoacenaphthylene with an internal alkyne, and does not require any organometallic reagent. A range of 1,2-disubstituted acenaphthylenes and 5,6-disubstituted 1,2-dihydrocyclopenta[f,g]acenaphthylenes were prepared in moderate to good yields. The method provides a rapid and simple route to dibenzo[j,l]fluoranthene through an Ullmann coupling. Georg Thieme Verlag Stuttgart New York.
Peri-interactions in 8-Diphenylphosphino-1-bromonaphthalene, 6-Diphenylphosphino-5-bromoacenaphthene, and derivatives
Beckmann, Jens,Do, Truong Giang,Grabowsky, Simon,Hupf, Emanuel,Lork, Enno,Mebs, Stefan
, p. 2233 - 2249 (2014/05/06)
The syntheses and full characterizations of the peri-substituted naphthalenes (Nap) and acenaphthenes (Ace) 1-Br-8-(Ph2P)-Nap (1a) and 5-Br-6-(Ph2P)-Ace (1b), as well as their derivatives 1-Br-8- [Ph2P(E)]-Nap [E = CH3 + (counterion I-) (2a); E = O (3a); E = S (4a); E = Se (5a)] and 5-Br-6-[Ph2P(E)]-Ace [E = CH 3 + (counterion I-) (2b); E = O (3b); E = S (4b); E = Se (5b)] are reported. In order to quantify the energetic and electronic effects of the peri-interactions, an additional set of molecules, 1c-5c, with the bromine atom and the Ph2P(E) fragment on opposite sides of the naphthalene group was generated, which serves as reference because 1c-5c exhibit negligible peri-interactions. The molecular arrangements of all 15 compounds were optimized at the B3PW91/6-311+G(2df,p) level of theory. The analysis of the peri-interactions was not only based on the inspection of the molecular arrangement and energies alone, but extended to a set of real-space bonding indicators (RSBI). These indicators were derived from theoretically calculated electron densities and pair densities, respectively. Particularly, the stockholder, Atoms-In-Molecules (AIM) and Electron-Localizability-Indicator (ELI-D) space partitioning schemes were used to produce Hirshfeld surfaces (HS), bond topological properties and basins of localized bonding and nonbonding electron pairs. Since 1c-5c are 35-58 kJ·mol-1 lower in energy than their counterparts 1a-5a, the hypothesis of a mainly repulsive peri-interaction in 1a/b-5a/b was confirmed. The shapes and contact patterns of the HSs of atoms and fragments involved in the peri-interactions (Br, P, E = CH3 +, O, S, Se) reveal that only in 1a and 1b are peri-interactions exhibited between the bromine and the phosphorus atoms. In all other cases (2a/b-5a/b), the interaction mainly occurs between the bromine atom and the E atom/fragment. According to the bond topological properties and the electron populations within the (non)bonding ELI-D basins, which both are almost unaffected by the Br-P/E periinteraction, sterical interactions are characterized essentially by geometrical and energetical changes.
Synthesis and crystallography of 8-halonaphthalene-1-carbonitriles and naphthalene-1,8-dicarbonitrile
Noland, Wayland E.,Narina, Venkata Srinivasarao,Britton, Doyle
scheme or table, p. 694 - 697 (2012/03/11)
A convenient and high-yielding three-step synthesis of 8-halonaphthalene-1- carbonitriles has been achieved by ring opening of 1H-naphtho[1,8-de][1,2,3] triazine with the corresponding halides as the key step. Naphthalene-1,8- dicarbonitrile also has been synthesised from 8-bromonaphthalene-1-carbonitrile via palladium-catalysed cyanation of the aryl bromide. The crystal structures of 8-chloronaphthalene-1-carbonitrile, the A polymorph of the bromo analogue, and naphthalene-1,8-dicarbonitrile are isomorphous with orthorhombic symmetry. The B polymorph of the bromo compound and the iodo analogue are also isomorphous, but with monoclinic symmetry. In all of the halo carbonitriles, the molecules are disordered with respect to the location of the halogen atoms and the nitrile groups. There are no intermolecular X...NC interactions in any of the solids.
Catalytic Sandmeyer bromination
Beletskaya, Irina P.,Sigeev, Alexander S.,Peregudov, Alexander S.,Petrovskii, Pavel V.
, p. 2534 - 2538 (2008/03/13)
An efficient catalyst system for Sandmeyer bromination is proposed. Aryl bromides and dibromides can be obtained with excellent yield by this synthetic protocol. Georg Thieme Verlag Stuttgart.
Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors
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Page/Page column 21; 22, (2010/11/29)
One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.
2,8'-Disubstituted-1,1'-Binaphthyls: A New Pattern in Chiral Ligands
Vyskocil, Stepan,Meca, Ludek,Tislerova, Iva,Cisarova, Ivana,Polasek, Miroslav,Harutyunyan, Syuzanna R.,Belokon, Yuri N.,Stead, Russel M. J.,Farrugia, Louis,Lockhart, Stephen C.,Mitchell, William L.,Kocovsky, Pavel
, p. 4633 - 4648 (2007/10/03)
The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 -> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 -> 19 and 18 -> 23). Racemic intermediate 22 was resolved by cocrystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).
Synthesis and Properties of 1,8-Di(2-thienyl)-, 1,8-Bs(5,2'-bithiophene-2-yl)-, 1,8-Bis(5,2':5',2''-terthiophene-2-yl)-, and 1,8-Bis(5,2':5',2'':5'',2'''-quaterthiophene-2-yl)naphthalenes and Related Compounds
Kuroda, Masami,Nakayama, Juzo,Hoshino, Masamatsu,Furusho, Noboru,Kawata, Takashi,Ohba, Shigeru
, p. 3735 - 3748 (2007/10/02)
1,8-Di(2-thienyl)-, 1,8-bis(5,2'-bithiophene-2-yl), 1,8-bis(5,2':5',2''-terthiophene-2-yl)-, and 1,8-bis(5,2':5',2'':5'',2'''-quaterthiophene-2-yl)naphthalenes (1a, 1b, 1c, and 1d, respectively) were synthesized starting from 1,8-dibromonaphthalene by application of NiCl2(dppp)-catalyzed coupling of aryl bromides with thienylmagnesium bromides.For comparison with these compounds, 1-(2-thienyl)-, 1-(5,2'-bithiophene-2-yl)-, 1-(5,2':5',2''-terthiophene-2-yl)-, and 1-(5,2':5',2'':5'',2'''-quaterthiophene-2-yl)naphthalenes (2a-d) were also prepared.Inspection of 1H and 13C NMR and UV/Vis data of 1a-d and 2a-d including X-ray single crystal structure data of 1b suggests that the planes of two oligothiophene units of 1a-d are approximately parallel to each other and are at large angles to the naphthalene ring.In accordance with these findings, CV oxidation potential data show that the radical cations formed from 1a-d are stabilized by intramolecular electron transfer interaction of the two oligothiophene units.
