New Synthetic Path to 2,2‘-Bipyridine-5,5‘-dicarbaldehyde and Its Use in the [3+3] Cyclocondensation with <i>trans</i>-1,2-Diaminocyclohexane

Hodačová, Jana; Budêšínský, Miloś

doi:10.1021/ol702612t

Cited by 35 publications

(27 citation statements)

References 11 publications

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“…The synthetic method providing such compounds relies on thermodynamically driven cycloimination of dialdehydes with vicinal diamines of the trans ‐1,2‐diaminocyclohexane or threo ‐1,2‐diphenyl‐1,2‐diaminoethane type . The first successful, quantitative synthesis of triangular hexaimine 1 ( trianglimine ), by Gawronski and coworkers, received a wide attention in scientific community as a convenient and efficient method for synthesis of poly‐aza macrocycles of different shapes and stoichiometry …”

Section: Introductionmentioning

confidence: 99%

Electronic and vibrational exciton coupling in oxidized trianglimines

Szymkowiak

Kwit

2017

Chirality

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Readily available chiral trianglimine and their (poly)oxygenated congeners represent a unique class of macrocyclic rigid compounds optimal for testing electronic and vibrational circular dichroism exciton chirality methods. Electronic and vibrational circular dichroism spectra of such trianglimines are strongly affected by polar substituents in macrocycle skeletons. Double substitution by OH groups in each aromatic fragment of the macrocycle causes sign reversal of the exciton couplet in the region of the strongest UV absorption. On the other hand, electronic circular dichroism spectrum of the macrocycle having 2 methoxy groups shows 2 exciton couplets-the long-wavelength positive and the second of the negative sign, observed at the shorter wavelengths. VCD spectra of macrocyclic imines show vibrational exciton couplets in the region of strong C=N stretches. The signs of these couplets are positive and the opposite of the diamine chirality. For trianglimine macrocycles the interpretation of VCD spectra in terms of excitons is much more convincing than for electronic circular dichroism spectra. By contrast, trans-1,2-diaminocyclohexane-based vicinal diimines, being a one-third of the respective macrocycle, do not exhibit any vibrational exciton effect. Experimental data were confronted with DFT calculations. We observed good-to-excellent agreement between experimental and computed data.

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Section: Introductionmentioning

confidence: 99%

Electronic and vibrational exciton coupling in oxidized trianglimines

Szymkowiak

Kwit

2017

Chirality

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“…Experimental procedure 2, 2′-Bipyridine-5,5′-dicarbaldehyde (bipy-CHO) was synthesized using reported procedure (Hodacova & Budesınsky, 2007). Then, bipy-1 was prepared by reacting 1 mmol of o-amino phenol with 2 mmol of 2,2′-bipyridine-5,5′-dicarbaldehyde in EtOH medium.…”

Section: Materials and Instruments Usedmentioning

confidence: 99%

Colorimetric detection of in situ metal acetates and fluorides by a bipyridyl‐linked Schiff base

Suganya

Park

et al. 2014

J of Molecular Recognition

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Here, we present a new bipyridyl moiety linked Schiff base (bipy-1) that is well characterized using spectroscopic techniques. Colorimetric and UV-vis titrations were used to study the photophysical properties of bipy-1 in the presence of various tetrabutyl ammonium salt of anions and metal salts containing different counter cations. bipy-1 showed selective recognition of dimethyl sulphoxide solution of tetrabutyl ammonium salt of F(-) ion accompanied with a UV-vis band at 529 nm and interesting binding of aqueous Co, Ni, and Cu acetates/fluorides, as confirmed by distinct color changes from fluorescent green to pink or orange and a strong band around 480-510 nm in the UV-vis spectrum. However, in the presence of Co, Ni, and Cu countercations, any form of metal acetate/fluorides was found to be able to respond to similar color changes from fluorescent green to pink or orange, showing a band around 480-510 nm. This type of output clearly indicates that the in situ formation of Co, Ni, and Cu acetates/fluorides also coordinates with bipyridyl nitrogen atoms.

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“…The field of the macrocyclic chemistry of metals is developing very rapidly due to its application [1][2][3] and importance of macrocyclic metal complexes in coordination chemistry [4] and bioinorganic chemistry [5]. Many universal macrocyclic ligands such as crown ethers [6], porphyrines, saturated and unsaturated polyamines [7][8][9], polyazmacrocyclic [10,11], N4S2 donor macrocyclic [12,13], Robson type tetraaminodiphenol macrocyclic ligands [14,15] have been reported in past few decades. The studies on complexes of Schiff base macrocyclic ligands with different size, number and donor atoms for coordination with variety of metal centers have been studies [16].…”

Section: Introductionmentioning

confidence: 99%