Oligothiophene-5,5-dioxides

G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, L. Antolini, O. Pudova, and A. Bongini, Oligothiophene 5,5-dioxides. Synthesis and electronic properties in relation to the parent oli-gothiophenes, J. Org. Chem., 63 5497-5506, 1998. 

Oligothiophene 5,5-dioxides can be regarded as D-A systems in which the sulfone group is rather electron withdrawing and represent the electron acceptor system in the oligomers. These 5,5-dioxide derivatives were generally prepared by peroxide-mediated oxidation of the thiophene sulfur using m-chloroperbenzoic... 

G. Sotgiu, M. Zambianchi, G. Barbarella, F. Aruffo, F. Cipriani and A. Ventola, Rigid-core fluorescent oligothiophene-5, 5 -dioxide iso thiocyanates. Synthesis, optical characterization and conjugation to monoclonal antibodies, J. Org. Chem., 68, 1512-1520 (2003). 

K. D. M. Harris, Solid-state supramolecular organization, established direcUy from powder diffraction data and photoluminescence efficiency of rigid-core oligothiophene-5,5-dioxides, J. Am. Chem. Soc., 125, 12277-12283 (2003). 

To keep the molecules far apart from each other and counteract aggregation, functionalization with bulky substituents is required. When soluble and larger sized all-oxidized oligothiophene-5,5-dioxides... 

Several studies of the trend of variation in PL intensity of oligothiophene-5,5-dioxides with solvent properties (including viscosity) confirm this assumption [42-44, 52-54],... 

Electroluminescence from green to near-IR has been demonstrated for oligothiophene-5,5-dioxides [63]. Figure 4.8 shows the electroluminescence spectra of compounds 3-5 (whose molecular shuctures are depicted in Scheme 4.2), 8 and 9 (whose molecular structures are depicted in Figure 4.6) and 11, whose molecular structure is shown in Figure 4.8, The electro-optical characteristics of all compounds are reported in Table 4.12. 

By combining electron-beam and soft lithography, including room-temperature nanoimprinting, one-dimensional planar photonic crystal (ID PhC) structures were realized with oligothiophene-5,5-dioxide 9 [77, 80], ID PhCs offer much more effective control of the device spectmm than external cavities and for this reason they are considered to be useful for the realization of electrically driven organic semiconductor lasers. 

A further study on the morphology and the photoresponse of blends of P3HT with oligothiophene-5,5-dioxide T50HM [87] (Figure 4.15) revealed the occurrence of a notable phase segregation between the two... 

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