Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety:  Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

Abstract

[structure: see text] A novel TTF-based donor with a uracil moiety, TTF-(1-n-butyluracil-5-yl) (TnbU), was synthesized. Crystal structures of both TnbU and the charge-transfer complex of TnbU-hydrogen cyananilate possess complementary double hydrogen bonds through uracil moieties and pi-stacking dimer structures between TTF skeletons. Furthermore, the TnbU-TCNQ charge-transfer complex shows a high electrical conductivity underlying the partial charge-transfer accompanied by a hydrogen-bonding interaction, which was substantiated in terms of the measurements of the IR, electronic spectra, and conductivity.

Activation of Hydrogen- and Halogen-Bonding Interactions in Tetrathiafulvalene-Based Crystalline Molecular Conductors

“…Two tetrathiafulvalenes bearing an uracil moiety have been described (Chart ), either fused on the TTF core as in o -Me 2 TTF[C(O)NHC(O)NH] or linked to the TTF core as in (1- n -butyluracil-5-yl)-TTF . In the former, of the two NH available for hydrogen bonding, one engages into the dimeric eight-membered cyclic motif while the other interacts strongly with a DMF solvate molecule, as shown in 2.33 .…”

Two-Dimensional Networks of Ethylenedithiotetrathiafulvalene Derivatives with the Hydrogen-Bonded Functionality of Uracil, and Channel Structure of Its Tetracyanoquinodimethane Complex

“…In addition to such a structural effect of the H-bond, we recently demonstrated new roles of the H-bonding interaction: control of electron-donating and -accepting abilities of donor/acceptor molecules and their molecular ratio in the CT complexes of the dibenzo-TTF derivative with amino groups 4 and the TTF derivative with imidazole systems . As part of our ongoing studies, we investigated TTF π-systems with nucleobases such as uracil and N 1 -butyluracil, TU and T n bU, and established the usefulness of the introduction of nucleobases into the TTF π-system to construct highly ordered multidimensional molecular systems based on complementary double H-bonds . Notably, achievement of high electrical conductivities in the tetracyanoquinodimethane (TCNQ) CT complexes of TU and T n bU showed an interesting strategy for the construction of H-bonded CT complexes .…”

Multifaceted Supramolecular Interactions from C‐Methylresorcin[4]arene Lead to an Enhancement in In Vitro Antibacterial Activity of Gatifloxacin

“…Participation of resorcin[4]arene and gatifloxacin individually in charge‐transfer process with electron‐deficient species is known . However, the present case represents a less known phenomenon, which involves an interplay between hydrogen bond and charge‐transfer interaction . Interestingly, there is no evidence of inclusion of any part of gatifloxacin in the macrocycle cavity, as was evident from the unaffected aromatic protons of RsC1.…”