An oligooxamacrocycle containing a π-donor tetrathiafulvalene and a π-acceptor quinone. Molecular and supramolecular structure

Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials

“…The X-ray analysis confirmed the trans substitution of the TTF, and revealed significant bending of the TTF framework, no doubt induced by the strained macrocyclic ring. [39] (This contrasts with the near-planar, strain-free TTF in macrocycle 6 [26] discussed above.) Analysis of the bond lengths [40] in the crystal structure of 22 [38] suggest a neutral (or near-neutral)…”

“…Macrocycle 6 containing both TTF and quinone moieties (synthesized via its dimethoxyphenyl precursor, similarly to 4 and 5) has been reported, [26] in which any charge transfer (if present at all) is almost certainly intermolecular rather than intramolecular. The X-ray crystal structure of 6 establishes that the TTF unit is cis-disubstituted, and the intramolecular planes of the TTF and quinone moieties do not overlap.…”

Donor−Acceptor Macrocycles Incorporating Tetrathiafulvalene and Pyromellitic Diimide: Syntheses and Crystal Structures

“…The configuration of the TTF unit in this cyclophane is cis and the two planes containing the TTF and quinone moieties in the crystal are nonoverlapping (orthogonal), suggesting that any charge-transfer interaction present in the crystal is intermolecular. [8] In this paper we present the synthesis of the TTFϪPMDI macrocycles 1 and 2, together with their crystal structures, as well as the synthesis of linear TTFϪPMDI derivatives 3 and 4. All compounds were synthesized using TTF derivatives containing aminoalkyl linkers.…”

Self-complementary azolophanes

“…Interest in self-complementary (donor-acceptor) cyclophanes arises for three main reasons: (1) they are suitable candidates for studying non-covalent interactions [1][2][3] such as chargetransfer (CT) and p-p stacking; (2) they are capable of undergoing self-organisation to form two or three dimensional supramolecular array in the solid state, 2,4 which results in channel and tubular structures at the nanoscale level; and (3) they could function as both exo and endo receptors simultaneously. 4 Staab et al 1,[5][6][7][8][9] and others 2,4,[10][11][12][13] have reported a variety of such self-complementary cyclophanes. Heterocyclic cyclophanes play a predominant role in hostguest chemistry and in particular, imidazole, benzimidazole and benzotriazole-based cyclophanes [14][15][16][17] (azolophanes) are considered as promising host molecules for inorganic ions as well as organic molecules.…”