The synthesis of new linear and angular systems useful as rigid rods and spacers in the design of molecules

Warrener, Ronald N.; Pitt, I. G.; Butler, Douglas N.

doi:10.1039/c39830001340

Cited by 46 publications

(23 citation statements)

References 3 publications

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“…In these systems, host preorganisation was achieved by using a bridged polycyclic linker. The favourable properties of fused [n]polynorbornyl scaffolds in molecular receptors, particularly with respect to host preorganisation, are reported in the literature by a number of research groups including those of Warrener and Butler, 7,[31][32][33][34][35][36][37][38][39] Paddon-Row, [40][41][42][43] Johnston, 19,[44][45][46] Pfeffer, [47][48][49][50][51][52][53] Clever, 47,50,54 and Margetić. [55][56][57][58] Importantly, tweezers 1 and 2 share a freely rotating phenyl diimide core inserted within the otherwise rigid polycyclic linker, a feature which allows unhindered adjustment of the interporphyrin distance, to potentially allow the binding of guests of different lengths.…”

Section: Introductionmentioning

confidence: 99%

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

et al. 2018

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The effect of the degree of conformational rigidity and/or flexibility on preorganisation in artificial molecular receptors continues to be actively explored by supramolecular chemists. This work describes a bis-porphyrin architecture, linked via a rigid polycyclic backbone, in which a sterically bulky 2,3,5,6-tetramethylphenyl diimide core restricts rotation to afford two non-interconvertible tweezer conformations; syn- and anti-. After separation, the host-guest chemistry of each conformation was studied independently. The difference in host geometry allows only the syn-conformation to form a strong 1 : 1 bis-porphyrin complex with the diamino ligand 1,4-diazabicyclo[2.2.2]octane (DABCO) (K11 = 1.25 × 108 M-1), with the anti-conformation adopting a 2 : 2 sandwich complex with DABCO (K22 = 5.57 × 1017 M-3).

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Section: Introductionmentioning

confidence: 99%

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

et al. 2018

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“…[33,34] Key steps are depicted in Scheme 2 and detailed www.chemeurj.org schemes and experimental procedures are presented in the Supporting Information. The norbornadiene dimer underwent a ruthenium-catalyzed thermal [2+2] cycloaddition of dimethyl acetylenedicarboxylate (DMAD), [35] followed by reduction of the esters to give hydroxyl groups protected with para-methoxybenzyl groups (PMB).…”

Section: Introductionmentioning

confidence: 99%

“…The exoisomer selectivity agrees with those reported previously for similar reactions. [34,36,37] The synthesis of the S-NB precursor was achieved by a similar procedure to the one used for L-NB. However, instead of treating 4 with cyclopentadiene to give the L-NB precursor, compound 4 was treated with quadricyclane to give the S-NB precursor.…”

Section: Introductionmentioning

confidence: 99%

Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Darwish

Eggers

Silva

et al. 2011

Chemistry A European J

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Herein, we describe the synthesis of straight (S) and L-shaped (L) norbornylogous bridges (NBs) with an anthraquinone moiety at the distal end as the redox-active head group and two thiol feet at the proximal end, by which the molecules assemble on gold surfaces. The NB molecules were shown to form self-assembled monolayers (SAMs) with a well-behaved surface redox process. The SAMs were characterized by using in situ IR spectroscopy, cyclic voltammetry, scanning tunnelling microscopy and electrochemical impedance spectroscopy. The surface selection rules associated with the IR band intensities allowed the estimation of the position of the anthraquinone moiety with respect to the surface and the tilt of the bridge with respect to the surface normal, both in pure and diluted monolayers. It is shown that the S- and L-NBs hold the plane of the anthraquinone moiety close to the surface normal or the surface tangent, respectively. Neither NB molecule changes its orientation if spaced by diluents on the surface. The difference in the structure of the S- and L-NB SAMs provides a suitable framework for the investigation of factors that govern electron transfer of anthraquinone moieties across self-assembled monolayers with limited structural ambiguity, as compared with the commonly used structurally flexible alkanethiol monolayers.

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“…Due to high regioselectivity and flexibility this methodology was employed for the synthesis of variety extended, rigid, rod-like norbornylogous molecules, similar to 94 or 96 [63,[65][66][67][68][69][70].…”

Section: P-benzoquinonementioning

confidence: 99%

Synthetic Chemistry of Quadricyclane

Петров¹,

Vasil'ev²

2006

COS

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The synthesis of new linear and angular systems useful as rigid rods and spacers in the design of molecules

Cited by 46 publications

References 3 publications

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Synthetic Chemistry of Quadricyclane

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