Sulfur-bridged chromophores for photofunctional materials: using sulfur oxidation state to tune electronic and structural properties

Abstract

In this perspective, the effect of different oxidation states in sulfur-bridged bichromophoric systems on structural, photochemical and photophysical properties in organic and coordination compounds is explored.

From Induced-Fit Assemblies to Ternary Inclusion Complexes with Fullerenes in Corannulene-Based Molecular Tweezers

“…For the above reasons, this design then allows us to determine the effect of the bridgehead group and the differential behavior between C 60 and C 70 recognition, if any. We provide a variety of motifs usually encountered in optoelectronic materials − from strong donors to typical acceptors. From a simplistic point of view, considering exclusively the electronic donor–acceptor properties of hosts and guests and chemical intuition, the best association with fullerenes would be found in N -tolyl carbazole 16 , whereas the worst one in ylidenmalononitrile 11-C­(CN) 2 .…”

Molecular Engineering of Chalcogen‐Embedded Anthanthrenes viaperi‐Selective C−H Activation: Fine‐Tuning of Crystal Packing for Organic Field‐Effect Transistors

“…Other catalysts such as [Cp*IrCl 2 ] 2 / AgSbF 6 , [Ru(p-cymene)Cl 2 ] 2 , and Pd(OAc) 2 did not deliver the desired product (Table S1, entries 6-8). After screening solvents, 2,2,2-trifluoroethanol (TFE) turned out to be the best (Table S1, entries [9][10][11][12][13][14][15][16][17]. Moreover, AgTFA worked better than the combination of Ag 2 CO 3 and TFA (Table S1, entry 18).…”

“…In addition, we further illustrate the transformation of p-type to n-type S-embedded anthanthrenes via the Satom oxidation to sulfone. [9] It is worthy of note that sulfone-based n-type materials originating from the oxidation of thiopyran-fused acenes remain undeveloped yet.…”

Tweaking the Optoelectronic Properties of S‐Doped Polycyclic Aromatic Hydrocarbons by Chemical Oxidation

“…In contrast, the other chalcogen atoms, S, Se, and Te atoms, feature a large multivalency space (from II to VI). [40] Thus, we conjectured that peri-thiaxanthenothiaxanthene (4 H ), the S-doped congener of PXX in which the O-atoms are replaced by S-atoms, [41,42] could be an ideal structural motif to engineer PAHs, whose optoelectronic properties are tailored by tweaking the chalcogen-atoms valency through oxidation (Figure 1). In particular, it is expected that mono-and di-oxidation of the S-atoms could be reflected in the widening of the molecular HOMO-LUMO gap, rising of the ionization potential and inducing a perturbation of the conformational properties that rule the solid-state organization.…”