FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W143903427> ?p ?o ?g. }

• W143903427 abstract "The science of non-planar p-conjugated carbon molecules, represented by C60 and the carbon nanotube, has been attracting great interest due to their potential utility over interdisciplinary fields, such as electrical materials science, catalysis, and pharmaceutics. In this context, bucky-bowls are now considered to be another group of key materials in the science of curved p-conjugated carbon systems. Most of the investigation in bucky-bowl chemistry has focused on C5v symmetric corannulene and its derivatives. However, the methods to prepare functionalized corannulenes are still limited because the rim of corannulene consists of aromatic double bonds. On the other hand, sumanene (1), a partial C3v symmetric structure of fullerenes, is characterized by three benzylic positions, which may allow facile functionalization. In 2003, a synthesis of 1 under nonpyrolytic conditions was developed by our group. Stereoselective trisilylation at the benzylic positions via the corresponding trianion was achieved to afford a single diastereoisomer. X-ray analysis showed columnar p-stacking in a concave–convex fashion, suggesting that 1 may be of potential utility as electrically active materials in the solid state. In order to develop sumanene-based bucky-bowl chemistry, the method for carbon–carbon bond formation at its benzylic positions is considered to be an urgent issue. In the present research, 1,2-addition of benzylic anions to various aldehydes was investigated to extend p-conjugation, which is also of interest in view of non-planar p-conjugated carbon chemistry. Herein, we describe the facile synthesis, characterization and DFT calculation of extended p-conjugation systems derived from sumanene. The condensation of the benzylic anions of 1 with aldehydes was investigated to extend p-conjugation of 1 (Table 1). Various bases were examined for the condensation with benzaldehyde. The use of aqueous 30% NaOH solution as a base in the presence of tetrabutylammonium bromide and a minimum amount of THF gave 2a quantitatively as both C3 symmetric and unsymmetric diastereomers. Several substituted benzaldehydes (for 2b–f) were employed for the condensation reaction to control the electronic state of the p-conjugated systems. Seven derivatives 2a–g with extended p-conjugation were successfully synthesized in 68% to quantitative yield (Table 1).§ Condensation with [2,29;59,20]terthiophene-5-carbaldehyde gave 2h. The structures of these derivatives were supported by H-NMR, C-NMR and FAB-TOF mass spectrometry (HRMS). The color of 2a–f was yellow in CH2Cl2 solution, whereas that of 2g and 2h was orange and red, respectively. The diastereomer ratio (C3 symmetric and unsymmetric ones) of 2b and 2c was approximately 1 : 3, which was determined by the peak area of the methyl and methoxy groups of 2b and 2c, respectively, in the H-NMR spectra. UV–vis and emission spectra of 2a–h were measured in several solvents. Table 2 summarizes the absorption maxima, emission maxima and HOMO–LUMO band gaps. UV–vis and emission spectra of 1, 2a, 2g and 2h in CH2Cl2 solution are shown in Fig. 1a and Fig. 1b. The absorption maxima lmax of 2a were observed at 345 and 457 nm assignable to p–p*, which are 67 and ca. 150 nm red-shifted, respectively, as compared with those of 1. On the other" @default.
• W143903427 created "2016-06-24" @default.
• W143903427 creator A5002589477 @default.
• W143903427 creator A5030768152 @default.
• W143903427 creator A5045501648 @default.
• W143903427 creator A5065220813 @default.
• W143903427 creator A5070347979 @default.
• W143903427 creator A5070724827 @default.
• W143903427 creator A5088720738 @default.
• W143903427 date "2007-01-01" @default.
• W143903427 modified "2023-09-27" @default.
• W143903427 title "Synthesis and characterization of p-extended bowl-shaped p-conjugated molecules{{" @default.
• W143903427 hasPublicationYear "2007" @default.
• W143903427 type Work @default.
• W143903427 sameAs 143903427 @default.
• W143903427 citedByCount "0" @default.
• W143903427 crossrefType "journal-article" @default.
• W143903427 hasAuthorship W143903427A5002589477 @default.
• W143903427 hasAuthorship W143903427A5030768152 @default.
• W143903427 hasAuthorship W143903427A5045501648 @default.
• W143903427 hasAuthorship W143903427A5065220813 @default.
• W143903427 hasAuthorship W143903427A5070347979 @default.
• W143903427 hasAuthorship W143903427A5070724827 @default.
• W143903427 hasAuthorship W143903427A5088720738 @default.
• W143903427 hasConcept C104779481 @default.
• W143903427 hasConcept C112613896 @default.
• W143903427 hasConcept C138716334 @default.
• W143903427 hasConcept C140205800 @default.
• W143903427 hasConcept C151730666 @default.
• W143903427 hasConcept C159985019 @default.
• W143903427 hasConcept C162862793 @default.
• W143903427 hasConcept C171250308 @default.
• W143903427 hasConcept C178790620 @default.
• W143903427 hasConcept C185592680 @default.
• W143903427 hasConcept C192562407 @default.
• W143903427 hasConcept C21951064 @default.
• W143903427 hasConcept C2779343474 @default.
• W143903427 hasConcept C2781314386 @default.
• W143903427 hasConcept C32909587 @default.
• W143903427 hasConcept C33347731 @default.
• W143903427 hasConcept C513720949 @default.
• W143903427 hasConcept C521977710 @default.
• W143903427 hasConcept C86803240 @default.
• W143903427 hasConceptScore W143903427C104779481 @default.
• W143903427 hasConceptScore W143903427C112613896 @default.
• W143903427 hasConceptScore W143903427C138716334 @default.
• W143903427 hasConceptScore W143903427C140205800 @default.
• W143903427 hasConceptScore W143903427C151730666 @default.
• W143903427 hasConceptScore W143903427C159985019 @default.
• W143903427 hasConceptScore W143903427C162862793 @default.
• W143903427 hasConceptScore W143903427C171250308 @default.
• W143903427 hasConceptScore W143903427C178790620 @default.
• W143903427 hasConceptScore W143903427C185592680 @default.
• W143903427 hasConceptScore W143903427C192562407 @default.
• W143903427 hasConceptScore W143903427C21951064 @default.
• W143903427 hasConceptScore W143903427C2779343474 @default.
• W143903427 hasConceptScore W143903427C2781314386 @default.
• W143903427 hasConceptScore W143903427C32909587 @default.
• W143903427 hasConceptScore W143903427C33347731 @default.
• W143903427 hasConceptScore W143903427C513720949 @default.
• W143903427 hasConceptScore W143903427C521977710 @default.
• W143903427 hasConceptScore W143903427C86803240 @default.
• W143903427 hasLocation W1439034271 @default.
• W143903427 hasOpenAccess W143903427 @default.
• W143903427 hasPrimaryLocation W1439034271 @default.
• W143903427 hasRelatedWork W1562053119 @default.
• W143903427 hasRelatedWork W1577866602 @default.
• W143903427 hasRelatedWork W1809239135 @default.
• W143903427 hasRelatedWork W1858917926 @default.
• W143903427 hasRelatedWork W1964798453 @default.
• W143903427 hasRelatedWork W1997258373 @default.
• W143903427 hasRelatedWork W2010720263 @default.
• W143903427 hasRelatedWork W2011590729 @default.
• W143903427 hasRelatedWork W2119431321 @default.
• W143903427 hasRelatedWork W2313895240 @default.
• W143903427 hasRelatedWork W2334925373 @default.
• W143903427 hasRelatedWork W2514753522 @default.
• W143903427 hasRelatedWork W2529076559 @default.
• W143903427 hasRelatedWork W2626475799 @default.
• W143903427 hasRelatedWork W2745041541 @default.
• W143903427 hasRelatedWork W2754262602 @default.
• W143903427 hasRelatedWork W2915025345 @default.
• W143903427 hasRelatedWork W2975888328 @default.
• W143903427 hasRelatedWork W3144729618 @default.
• W143903427 hasRelatedWork W3159062914 @default.
• W143903427 isParatext "false" @default.
• W143903427 isRetracted "false" @default.
• W143903427 magId "143903427" @default.
• W143903427 workType "article" @default.