A complementary disk-shaped π electron donor–acceptor pair with high binding affinity

Abstract

Hexaazatriphenylene triimides (HAT) have been shown to be a novel class of disk-shaped p electron acceptors that pair with donors with complementary shape and electron demands, such as triphenylene (TP) derivatives. The donor-acceptor (DA) pair forms a strong charge-transfer complex in CH 2 Cl 2 with an association constant of 2.6 Â 10 4 M À1 , which is remarkable for a recognition system that is solely based on electrostatic interactions between two p systems. NMR studies, along with molecular modelling, have revealed a complementary charge distribution and an ''eclipsed'' conformation in the DA complex. The strong DA interaction results in extended alternating DA stacks in the thin film and mesophases.

Donor–acceptor cocrystal based on hexakis(alkoxy)triphenylene and perylenediimide derivatives with an ambipolar transporting property

“…In our experiment, we did not observe obvious color change after blended H6TP into EP-PDI solution. The phenomenon was unlike that reported in the literatures 13 Fluorescence emission spectrum was also performed for further study, as shown in Figure 5b. A wide emission peak at 386 nm was observed in H6TP solution, when excited at 300 nm.…”

“…13 We have also obtained 1 H NMR spectra of H6TP, EP-PDI and H6TP/EP-PDI (1/1) in CDCl 3 , which were shown in Figure 5c.…”

Stimuli‐Responsive Self‐Assembly of a Naphthalene Diimide by Orthogonal Hydrogen Bonding and Its Coassembly with a Pyrene Derivative by a Pseudo‐Intramolecular Charge‐Transfer Interaction

“…23 The association constant ( K ) of the CT complex was estimated to be 0.6×10 4 M −1 by concentration‐dependent UV/Vis spectroscopic experiments (see Figure S11) 24. Such a high value has rarely been reported for intermolecular D–A complexes25 and can be attributed to the synergistic assistance of multiple H‐bonding interactions (Figure 1) in stabilizing the CT state. Interestingly, equimolar 1 + 2 ( c =2 m M ) prepared by half‐dilution of a concentrated mixture was significantly more red in color than the mixture prepared directly at 2 m M (Figure 5 c).…”

Multi‐Responsive Supramolecular Gels Based on Charge Transfer Interactions

“…In order to preparerobust D-A gels and reduce the influence of other driving forces, we envisage that it is essential to import intensiveC Ti nteractions into the gelation system.T o this end we employed two C 3 -symmetricm olecules, i.e., Dtype triphenylene and A-type hexaazatriphenylenet riimide (Scheme 1), which can form stable complext hrough CT interactions owing to their extendeda romatic cores, perfect complementary electronic characters,a nd similar molecular structures. [13] The vertices of both triphenylene and hexaazatriphenylene triimide were modifiedw ith relatively long alkyl chains (-C 16 H 33 ,t he derivatives were denoted by TP and HAT, respectively)t oi ncrease the solubility,a sw ell as to facilitate the gelation by immobilizingm ore solvent. Upon mixing the solutions of TP (colorless) and HAT( pale yellow) in chloroform, toluene or xylene,t he mixture immediatelyt urned deep purple (Figures S1 and S2), indicating the formation of the CT complex.…”

“…Hence, it appeared that the nanofibers in the sponge-like gel were formed by face-to-face stacking of HATa nd TP molecules, which was in agreement with the previousc onclusion derived from molecular modelling. [13] The sponge-like gel was highly sensitive to mechanical or thermalt reatment. For instance, the gel dissociated after sonication for ca.…”