Bicyclic Structures Prohibiting the Walden Inversion. Further Studies on Triptycene and its Derivatives, Including 1-Bromotriptycene<sup>1</sup>

Bartlett, Paul D.; Lewis, Edward S.

doi:10.1021/ja01158a094

Cited by 63 publications

(22 citation statements)

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“…1,2 In this respect, especially triptycene was investigated in depth 3,4 and already early reports describe spectroscopic differences between triptycene and triphenylmethane, which can only be explained by homoconjugation effects. 5 It was in 1983 when Martin et al used photoelectron spectroscopy in combination with theoretical calculations to finally prove the existence of homoconjugation. 6 These findings have been picked up more recently by studies on dialkoxytriptycenes and their oxidations to the corresponding quinones by Rathore and coworkers in solution and in silico.…”

Section: Introductionmentioning

confidence: 99%

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

et al. 2021

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Homoconjugation is a phenomenon discussed for various π-systems where classical conjugation is broken by e.g. methylene units but still a stabilization by electronic communication exists. In this respect, triptycene with its rigid C3 symmetric geometry is an ideal scaffold to study this phenomenon. Although several studies based on triptycene strengthen the hypothesis of homoconjugation, in all described cases the electronic communication through space relies on different π-blades. Here, two triptycenes are presented having the exact same π-extended chromophore, but differently annulated to the bicyclic core. Both compounds were investigated by spectroscopic as well as computational means and compared with the corresponding model compound, elucidating the influence of the attachment site to the triptycene core on potential homoconjugation.

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Section: Introductionmentioning

confidence: 99%

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

et al. 2021

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“…6), transannular electronic interaction between the remote (nonconjugated) benzene rings has been of particular interest and still remains a matter of controversy (Ref. 7).…”

Section: Introductionmentioning

confidence: 99%

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

Murata¹

1983

Pure and Applied Chemistry

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-The group theoretical analysis of the electronic structure of l,4-dihydro-l,4-bis (dicyanoinethylene)triptycene leads to an interesting but rarely documented notion, "charge transfer transition for symmetry forbidden charge transfer interaction" , which was supported by the substituent effects on the charge transfer band shifts. The substituent effects on the charge transfer band shifts were also observed in a series of 9,lO-dihydro-9, l0-o-benzenoanthracene-l,4-diones. These results provide decisive evidence for the fact that the orbitals involved in the ground state charge transfer interaction need not be the same as those involved in the charge transfer transition. In general, charge transfer phenomena between donor and acceptor components fixed in the rigid frameworks of C2v and C5 point groups are also discussed by means of the symmetry properties of the interacting orbitals.

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“…6 To immobilize triptycene, we designed and synthesized a 9-substituted derivative that provides a point of attachment at the bridgehead, maintaining the C 3 symmetry. 7 Although triptycene has been extensively modified for use in materials chemistry applications, 8 functionalization at the C9-position of triptycene has rarely been reported. 9 …”

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confidence: 99%

Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting

et al. 2016

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Triptycenes have been shown to bind nucleic acid three-way junctions but rapid and efficient methods to diversify the triptycene core are lacking. An efficient synthesis of a 9-substituted triptycene scaffold is reported that can be used as a building block for solid-phase peptide synthesis (SPPS) and rapid diversification. The triptycene building block was diversified to produce a new class of tripeptide-triptycenes and their binding abilities toward d(CAG)·(CTG) repeat junctions were investigated.

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Bicyclic Structures Prohibiting the Walden Inversion. Further Studies on Triptycene and its Derivatives, Including 1-Bromotriptycene¹

Cited by 63 publications

References 1 publication

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting

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Bicyclic Structures Prohibiting the Walden Inversion. Further Studies on Triptycene and its Derivatives, Including 1-Bromotriptycene1

Cited by 63 publications

References 1 publication

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting

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Bicyclic Structures Prohibiting the Walden Inversion. Further Studies on Triptycene and its Derivatives, Including 1-Bromotriptycene¹