Synthesis and characterization of dehydrothieno[18]annulenes

Sarkar, Abhijit; Haley, Michael M.

doi:10.1039/b004962j

Cited by 34 publications

(36 citation statements)

References 14 publications

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“…This result is in agreement with the higher overall π-conjugation [26] in complexes containing 2,5T (λ max = 331 nm) [27] as compared to those of 2,4T (λ max = 277 nm). E 1/2 (ox) and E 1/2 (red) for 1 are very similar to those of the corresponding 2,5T derivative, indicating that the position of the -C 2 SiMe 3 substituent on the thiophene ring does not have a significant influence on the electrochemical processes.…”

Section: Electrochemistry Of 1 Andsupporting

confidence: 93%

“…This seems to indicate that the HOMO (depopulated by oxidation) of the 2,5T derivatives shows a greater π-delocalization than the HOMO of the 2,4T derivatives and than the LUMO (populated by reduction) in both groups, in agreement [26] with the higher conjugation observed in 2,5T derivatives, where the λ max value is less blue-shifted relative to that of 2,4T compounds. The differences in ∆E 1/2 indicate a significant contribution of through-bond electronic interactions as compared to through-space ones in these compounds.…”

Section: Electrochemistry Of 2ј and 4-9supporting

confidence: 80%

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Synthesis, Characterization, Structures and Comparative Electrochemical Study of 2,4‐Bis(trimethylsilylethynyl)thiophene Coordinated Carbonylcobalt Units

et al. 2007

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The reaction between 2,4-dibromothiophene and trimethylsilylacetylene (TMSA) in the presence of Pd(PPh 3 ) 4 , CuI and triethylamine gave rise to the formation of 2,4-bis(trimethylsilylethynyl)thiophene (2,4T) and 4-bromo-2-(trimethylsilylethynyl)thiophene (2,4TЈ). Complexes 1, 2, 3 or 1Ј were obtained by direct reaction between Co 2 (CO) 8 and 2,4T or 2,4TЈ, respectively. (Diphenylphosphanyl)methane-substituted alkyne carbonyl complexes 4, 5, 6 and 2Ј were prepared by substitution reaction of carbonyl ligands in the presence of Me 3 NO at the Co 2 (CO) 6 units of 1, 2, 3 and 1Ј, respectively. Desilylation of the non-metallated and metallated al-

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Section: Electrochemistry Of 1 Andsupporting

confidence: 93%

Section: Electrochemistry Of 2ј and 4-9supporting

confidence: 80%

Synthesis, Characterization, Structures and Comparative Electrochemical Study of 2,4‐Bis(trimethylsilylethynyl)thiophene Coordinated Carbonylcobalt Units

et al. 2007

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“…Compounds such as 106 [51] and 107 [52] have been prepared to study their optical properties and thus possibly increase the polarizability of the basic [18]annulene system. Dimethyldihyrodropyrene-fused hybrid 108 has been used as an NMR probe of aromaticity in DBAs.…”

Section: Dba Hybridsmentioning

confidence: 99%

Synthetic Strategies for Dehydrobenzo[n]annulenes

2003

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Dehydrobenzoannulenes have accrued great interest due to their potential uses such as hosts for binding guest molecules and precursors to fullerenes and other carbon‐rich materials, as well as their unique properties such as conductivity or superconductivity and nonlinear optical effects. These systems have seen numerous synthetic strategies employed in their construction over the past 50 years. As alkyne chemistry has developed more recently, annulene networks with greater complexity have been possible and the field has seen a vast resurgence. This article gives an account of synthetic methods developed for the preparation of annulenic systems and describes some of the interesting observed properties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…The X‐ray data (CCDC: 1119562, 148 b ) are not sufficient to discuss the bond angles of the alkynes. Haley and co‐workers synthesized π‐expanded thiophene‐fused macrocycles 149 , but this series is strain free . Haley and co‐workers synthesized thiophene‐fused strained dehydroannulenes 150 by using intramolecular Eglinton diyne formation .…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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Synthesis and characterization of dehydrothieno[18]annulenes

Abstract: Use of a palladium/copper alkyne cross-coupling strategy provides access to three tris(thiophene-fused) dodecadehydro[18]annulenes, including examples of both highly symmetrical C 3h and unsymmetrical C s structures.

Cited by 34 publications

References 14 publications

Synthesis, Characterization, Structures and Comparative Electrochemical Study of 2,4‐Bis(trimethylsilylethynyl)thiophene Coordinated Carbonylcobalt Units

Synthesis, Characterization, Structures and Comparative Electrochemical Study of 2,4‐Bis(trimethylsilylethynyl)thiophene Coordinated Carbonylcobalt Units

Synthetic Strategies for Dehydrobenzo[n]annulenes

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

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