Star‐Shaped Molecules Containing Polyalkynyl Groups with Metal Moieties on Benzene and Triphenylene Cores

Huang, Chiung-Cheng; Lin, Ying‐Chih; Lin, Ping-Yu; Chen, Yu‐Ju

doi:10.1002/ejoc.200600380

Cited by 14 publications

(5 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, they were employed to design new ligands for multimetal complexes [131,230,231,232,233,234]. Especially the cobalt complexes, were subsequently used to prepare carbon nanomaterials by pyrolysis [235].…”

Section: Star Compounds With a Benzene Corementioning

confidence: 99%

“…Hexakisoligo(phenylene ethynylene)benzene Derivatives (C-6-A-8): As mentioned for the hexaphenylbenzene cores, hexa(phenylethynyl)benzene scaffolds are often prepared to utilize their defined and persistent shape. For example, they were employed to design new ligands for multimetal complexes [ 131 , 230 , 231 , 232 , 233 , 234 ]. Especially the cobalt complexes, were subsequently used to prepare carbon nanomaterials by pyrolysis [ 235 ].…”

Section: Star Compounds With a Benzene Corementioning

confidence: 99%

“…The synthesis of compounds 129 - 131 is illustrated in Scheme 37 . Although many synthetic strategies allow the preparation of symmetrically substituted triphenylenes [ 331 ], all members of this molecular family were obtained in a semi divergent/convergent approach [ 209 , 211 , 234 , 332 ]. In all cases 2,3,6,7,10,11-hexabromotriphenylene was converted in a convenient transition metal catalyzed cross-coupling reaction, in which six arms were attached.…”

Section: Condensed Ring Systems As Coresmentioning

confidence: 99%

“…Huang et al . synthesized triphenylenes with 2-(4-ethynylphenyl)ethynyl arms [ 234 ]. Upon complexation with the transition metal entities the absorption and fluorescence spectra were bathochromocally shifted by a simultaneous decrease of the fluorescence quantum yield.…”

Section: Condensed Ring Systems As Coresmentioning

confidence: 99%

See 3 more Smart Citations

Star-Shaped Conjugated Systems

2010

View full text Add to dashboard Cite

The present review deals with the preparation and the properties of star-shaped conjugated compounds. Three, four or six conjugated arms are attached to cross-conjugated cores, which consist of single atoms (B, C+, N), benzene or azine rings or polycyclic ring systems, as for example triphenylene or tristriazolotriazine. Many of these shape-persistent [n]star compounds tend to π-stacking and self-organization, and exhibit interesting properties in materials science: Linear and non-linear optics, electrical conductivity, electroluminescence, formation of liquid crystalline phases, etc.

show abstract

Section: Star Compounds With a Benzene Corementioning

confidence: 99%

Section: Star Compounds With a Benzene Corementioning

confidence: 99%

Section: Condensed Ring Systems As Coresmentioning

confidence: 99%

Section: Condensed Ring Systems As Coresmentioning

confidence: 99%

See 2 more Smart Citations

Star-Shaped Conjugated Systems

2010

View full text Add to dashboard Cite

show abstract

“…Only a few reports on the extension of conjugation of the triphenylene chromophore have appeared. 2,3,6,7,10,11-Hexakis(ethynyl)triphenylene derivatives have been used in photonics as organic light emitting diode (OLED) materials [40–42]. Therefore, it is worthwhile to tune the fluorescence emission of the triphenylene chromophore by the addition of suitable substituents.…”

Section: Introductionmentioning

confidence: 99%

Donor-acceptor substituted phenylethynyltriphenylenes – excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission

Nandy¹,

Sankararaman²

2010

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummarySeveral 2-(phenylethynyl)triphenylene derivatives bearing electron donor and acceptor substituents on the phenyl rings have been synthesized. The absorption and fluorescence emission properties of these molecules have been studied in solvents of different polarity. For a given derivative, solvent polarity had minimal effect on the absorption maxima. However, for a given solvent the absorption maxima red shifted with increasing conjugation of the substituent. The fluorescence emission of these derivatives was very sensitive to solvent polarity. In the presence of strongly electron withdrawing (–CN) and strongly electron donating (–NMe2) substituents large Stokes shifts (up to 130 nm, 7828 cm−1) were observed in DMSO. In the presence of carbonyl substituents (–COMe and –COPh), the largest Stokes shift (140 nm, 8163 cm−1) was observed in ethanol. Linear correlation was observed for the Stokes shifts in a Lippert–Mataga plot. Linear correlation of Stokes shift was also observed with E T(30) scale for protic and aprotic solvents but with different slopes. These results indicate that the fluorescence emission arises from excited state intramolecular charge transfer in these molecules where the triphenylene chromophore acts either as a donor or as an acceptor depending upon the nature of the substituent on the phenyl ring. HOMO–LUMO energy gaps have been estimated from the electrochemical and spectral data for these derivatives. The HOMO and LUMO surfaces were obtained from DFT calculations.

show abstract