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Relevant academic research and scientific papers

Spacer length dependent architectural diversity in bis-dipyrrin copper(II) complexes

A series of copper(ii) complexes (1-9 and 3′) derived from bis-dipyrrin ligands (L1-L9 and L3′) with diverse spacer lengths [-(CH2)n-] have been described. Structural diversities in these complexes have been explicitly established by spectral and structural studies on these and a closely related nickel(ii) complex (3′′). All the ligands and complexes have been thoroughly characterized by spectroscopic studies (ESI-MS, IR, 1H, 13C NMR, UV/vis) and structures of 2, 3′, 3′′, 6, 8 and 9 were determined by X-ray single crystal analyses. It has been unambiguously established that ligands with n ≤ 6 gave heteroleptic binuclear (1-5), while those with n ≥ 7 yielded homoleptic mononuclear (6-9) bis-dipyrrinato complexes. Spectral and structural studies revealed distorted square planar (1-5) and distorted tetrahedral geometries (6-9) about the copper(ii) centre in these complexes which has further been evidenced by EPR and electrochemical studies. Structural differences based on the odd and even number of methylene spacers in these complexes have been supported by DFT studies. A line between the syn- and anti-conformations of the complexes has been drawn on the basis of a limiting spacer length.

Hexahelicenophanes

A reaction sequence was studied for the preparation of cyclophanes 12, which contain 2,7-bis(2-phenylethenyl)naphthalene chromophores and polymethylenedioxy chains of different length. The irradiation of 12 in the presence of I2 led then, by ox

Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds

Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright

Highly efficient ring closure of aromatic dialdehydes to macrocyclic allenes

The one-pot double deoxygenation of simple alkyl- and polyether-tethered aromatic dialdehydes to give macrocyclic allenes has been accomplished in extraordinarily high yield without the need for slow-addition techniques, using a Ti(IV)-substituted ylide reagent and bis(trimethylsilyl)amide bases. Diastereoselective allene formation occurs when a binaphthyl unit is present in the substrate backbone, and the resulting cyclic allene is characterized by X-ray diffraction. Highly efficient cyclization is proposed to be the result of a combination of preorganization about the amide base counterion and a low concentration of the immediate precursor to Wittig-style olefination ring closure.

Investigation of the one-flask synthesis of porphyrins bearing meso-linked straps of variable length, rigidity, and redox activity

The reactions of 18 dialdehydes have been examined in the two-step one-flask room temperature porphyrin synthesis. Efficient alkylation methods were established for the reaction of diols and diacids with bromomethylbenzaldehyde. Dialdehydes linked at the o,o'- or m,m'-positions were converted to strapped porphyrins in yields up to 25%, while the one p,p'-linked dialdehyde that was examined failed to give porphyrin. The resulting porphyrins bear straps joining adjacent, meso-positions rather than across the face of the porphyrin. Dialdehydes incorporating rigid groups provided improved yields in some but not all cases. The yield of strapped porphyrin exhibited a maximum at 10-2 M reactant concentrations. The o,o'-strapped porphyrins exist as atropisomers that are sufficiently stable to interconversion at room temperature to be separable chromatographically. No atropisomers of m,m'-strapped porphyrins could be separated, though some could be observed by 1H NMR spectroscopy. For two different m,m'-strapped porphyrins, the ΔG values for interconversion of the atropisomers were found to be 66 and 68 kJ/mol. The outer rings in these strapped porphyrins range in size from 14 to 24 atoms. Five porphyrins with bridging redox-active groups (ferrocene or anthraquinone) have been prepared in one-flask reactions, including a porphyrin bearing one ferrocene and one anthraquinone in straps across adjacent meta-substituted phenyl sites.

Intramolecular Cycloadditions with Carbonyl Ylides: From Oxiranes to Large Ring Systems

Within the classes of 1,3-dipoles intramolecular cycloaddition reactions with carbonyl ylides, accessible by heating of the oxirane precursors 4-10, are studied for the first time in a systematic manner.Although the formation of the corresponding fused and/or bridged tetrahydrofuran derivatives (32-34, 44-46, 50-63) has been established in all cases with the exception of 4e and 6a, the rate of formation as well as the yield of the cycloadducts depend strongly on the dipolarophilicity of the olefinic component: Whereas non-activated C=C bonds undergo the cycloaddition step slowly and only when being arranged in a relatively close position to the dipole unit (the maximum size of the second ring, formed by "tieing": 9-membered), ene-oxiranes with an electron deficient double bond are reacting much faster and (in contrast to cycloadditions so far known for other 1,3-dipoles) also at a large distance between the ?-centers.In this way macrocycles with up to 34 ring members have been obtained.This high regio- and stereoselectivity observed in most cases of the cycloadditions is explained mainly by steric factors.

Both-faces Hindered Porphyrins. Part 1. Synthesis and Characterization of Basket-handle Porphyrins and Their Iron Complexes

The synthesis of the 'both-faces' hindered porphyrins using two different methods is reported.These so-called 'basket-handle' porphyrins (BHP) are derived from 5,10,15,20-tetraphenylporphyrin in which two opposite phenyl groups are bridged by alkylene or arylene-p-bisalkylene chains.In addition to the desired compounds , two other isomers were obtained .These were separated by t.l.c. on silica gel and then individually characterized.The structural assignment of the three isomers in the five series studied was based on the 1H n.m.r. spectra of the free bases and of their iron(II) complexes.