Nitrogen-doped molecular bowls as electron donors in photoinduced electron transfer reactions

Abstract

In recent years, the chemistry of curved -conjugated molecules has experienced a sharp rise. The inclusion of a heteroatom in the carbon network significantly affects its semiconducting properties. In this...

The Hunter Falls Prey: Photoinduced Oxidation of C60 in Inclusion Complex with Perfluorocycloparaphenylene

“…It can be assumed that PF[10]CPP⊃C 60 complex is formed in solution, since fullerene complexes with a noticeably lower interaction energy are known. For example, ΔE int for the complex of C 60 with π‐extended corannulene bowl is only −31 kcal/mol, [29a] but the existence of such a complex in solution has been established experimentally [29b] . The dispersion interactions play a major role in the stability of the complex, as shown earlier for systems of a similar nature [11c,30] .…”

Aromaticity controls the excited-state properties of host–guest complexes of nanohoops

“…24,25 It is known that the introduction of heteroatoms into a π-conjugated system of carbon atoms can dramatically affect its properties. 26,27 Doping with nitrogen or boron atoms influences the semiconducting and luminescent properties of organic molecules due to changes in the band structure. 28 Doping antiaromatic hydrocarbons with nitrogen leads to an increase in their electron-withdrawing ability.…”

Excited State Processes in Supramolecular Complexes of Cyclic Dibenzopyrrolopyrrole Isomers with C60 Fullerene

“…Typically, the solvation energies of the CT states are much higher than those of the GS or LE states due to the polarity of the systems. However, our previous investigations show that for fullerene complexes with various carbon‐rich hosts, such as bowl‐shaped molecules, [19] CPPs and their π‐extended analogs, the solvation energy of the CT states is only slightly different from the energy of the GS [41–44] . For the [ 4 ] DHPP⊃C 60 complexes, a difference in the dipole moments (Δμ) for CT1 and GS states was found in the range from 1.8 to 12.6 D. Taking into account that the GS→CT1 transition corresponds to the HOMO‐to‐LUMO transition, the observed range of the dipole moment changes is fully consistent with the HOMO localization on the [ 4 ] DHPP fragment.…”

“…The number of BCPs depends on the stereoisomer of the nanoring. In general, the [4]DHPP�C 60 complexes with aromatic units are characterized by a larger number of BCPs (22)(23) than the [4]PP�C 60 complexes (18)(19)(20). Taking into account that the characteristics of BCPs are quite similar for [4]DHPP�C 60 and [4]PP�C 60 (Table S5), the greater number of BCPs found in [4]DHPP�C 60 correlates well with their higher stability compared to [4]PP�C 60 .…”

“…[16] It is known that heteroatoms in a carbon π-conjugated system can drastically change its properties. [17][18][19] Doping with nitrogen or boron atoms changes the band structure of organic molecules, thereby modulating their semiconductor and luminescent properties. [20][21][22] Nitrogen atoms in antiaromatic hydrocarbons increase their electron-withdrawing ability.…”