Molecular design of benzothiadiazole-based dyes for working with carbon nanotube photocatalysts

Ferrocenyl‐Pyrenes, Ferrocenyl‐9,10‐Phenanthrenediones, and Ferrocenyl‐9,10‐Dimethoxyphenanthrenes: Charge‐Transfer Studies and SWCNT Functionalization

“…Ferrocene‐functionalized CNT nanohybrids have attracted much attention in the fields of (bio)analytical electrochemistry, solar energy conversion, or as electrocatalytically active materials and photosensitizers, whereby the modification can be achieved by exohedral functionalization at the CNTs surface or in an endohedral fashion by filling the nanotubes with ferrocene species . Exohedral covalent attachment of ferrocenes to SWCNTs is thereby better considered as non‐covalent binding.…”

“…[29] Such arrangements allow,f or example, tuning of the transistor channel in nanoelectronic SWCNT field-effect transistors, which enables the fabrication of optoplasmonic sensor arrays on the chip level. [29,30] Ferrocene-functionalized CNT nanohybrids have attracted much attentioni nt he fields of (bio)analytical electrochemistry, [31] solar energy conversion, [32] or as electrocatalytically active materials [33] and photosensitizers, [34] whereby the modification can be achieved by exohedral functionalization at the CNTss urface [31,35,36] or in an endohedral fashionb y filling the nanotubes with ferrocene species. [37][38][39][40] Exohedral covalenta ttachment of ferrocenes to SWCNTsi st hereby betterc onsidered as non-covalent binding.…”

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

“…45 The increased Stokes' shift in more polar solvent suggests that the excited state of pH-BTZ has a higher dipole moment than its ground state, indicating a redistribution of charge following photoexcitation and the formation of an intramolecular charge transfer state. [46][47][48] A linear relationship between the observed Stokes' shift and solvent polarity was also attained when the Reichardt E T (30) parameter was used as an alternative measure of solvent polarity (see Fig. S59 ‡).…”

“…5 While there has been selected reports of homogeneous BTZ photocatalysis arising from intramolecular charge transfer between the donor and acceptor units, there has been no indepth exploration of how their photophysical properties and excited state redox potentials can be altered by manipulating available structural levers. [30][31][32][33][34][35] The reaction that was selected to test this library of BTZ photocatalysts was the decarboxylative C-H functionalisation of heteroarenes, previously explored by Glorius and coworkers. 36 This Miniscitype reaction was noted to provide a direct method to alkylate a wide variety of substrates, including pharmaceutical analogues, using visible light and without the need for prefunctionalisation of substrates.…”

Palladium-Catalyzed Direct (Het)arylation Reactions of Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole and 4,8-Dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)

“…A combination of reagents, including Pd(OAc) 2 , tricyclohexylphosphine tetrafluroborate salt (Cy 3 PHBF 4 ), sodium tert-butoxide and neodecanoic acid was effective for the synthesis of 4,7-bis(5-hexyl-2-thienyl)benzo[c][1,2,5]thiadiazole [27]. tris-(Dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) together with potassium pivalate as a base and tris(o-methoxyphenyl)phosphine as a ligand was successfully employed for arylation of 4,7-dibromobenzo[c]thiadiazole [28][29][30][31]. Thiazolyl derivatives of benzo[c][1,2,5] thiadiazole were prepared in good yields using palladacycle Herrmann complex (transdi(µ-acetato)-bis[o-(di-o-tolylphosphino)-benzyl]dipalladium(II)), cesium pivalate as base and tris(o-methoxyphenyl)phosphine as ligand [32].…”