Recent Advances in Using Transition-Metal-Catalyzed C–H Functionalization to Build Fluorescent Materials

Abstract

Organic fluorescent molecules have broad applications in modern technology, such as in security systems, chemosensors, bioprobes, field-effect transistors, memory devices, organic light-emitting diodes, etc. The transition-metal-catalyzed C-H bond functionalization approach represents a distinct, facile, and atom-efficient tactic for the construction of organic fluorescent molecules, which are often difficult to prepare using typical synthetic methods. In this review, four types of C-H bond functionalization reactions for the preparation of fluorescent materials are discussed: (1) transition-metal-catalyzed C-H/C-X cross-coupling reactions; (2) transition-metal-catalyzed C-H/C-H cross-coupling reactions; (3) transitionmetal-catalyzed C-H addition and/or annulation reactions; and (4) transition-metal-catalyzed C-H/C-M or C-H/Het-H bond functionalization. The objective of this review is to characterize the current state of the art in using transition-metal-catalyzed C-H functionalization to build fluorescent molecules as well as their application in electroluminescent materials, mechanofluorochromic materials, labels, sensors for bioimaging, etc.

Harnessing sulfur and nitrogen in the cobalt(iii)-catalyzed unsymmetrical double annulation of thioamides: probing the origin of chemo- and regio-selectivity

“…Likewise, the ester linked biologically relevant motifs 8g and 8n also show intense emission bands and could be useful as fluorescent drug carriers as well as fluorescent probes for cell imaging. 50 The enhanced fluorescence properties of π-extended scaffolds 5o and 5q with a longer life time 70 (3.42 ns for 5o ; Fig. 5D ) are notable and could be applicable for potential material applications.…”

“…In general, the extended π-conjugation largely contributes to the tuning of the photophysical properties of the molecular skeleton. 50 Thus, anthracene- and carbazole-anchored thiopyrano-isoquinolines 3y (70%) and 3z (84%) were successfully prepared ( Scheme 1c ). Meanwhile, the tetra -annulation (two consecutive double annulations) of pre-functionalized 4,4′-aryldithioamides with 2a led to structurally diverse linear ( 4a , 52%) and ‘V-shaped’ ( 4b , 61%) polyaromatics ( Scheme 1d ).…”

Rhodium‐Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds

“…As is widely known, organic fluorescent molecules have broad applications in chemosensors,organic light-emitting diodes,field-effect transistors,m emory devices,a nd bioprobes etc. [16] In addition, triphenylamine (TPA) derivatives are considered versatile materials because they possess nonplanar characteristics, excellent electron-donating properties,and hole-transporting capability. [17] Therefore,w ed esigned and synthesized three triphenylamine (TPA) derivatives containing organic fluorescent molecules (10)(11)(12)t hrough ap rogrammed rhodiumcatalyzed dealkenylative arylation and C À Ha rylation, and palladium-catalyzed Suzuki-Miyaura reaction of 1h with different arylboronic acids (Scheme 4, see also Supporting Information for details).…”

Sulfur Versus Nitrogen Chelation in C-H Activation: Cobalt(III)-Catalyzed Unsymmetrical Double Annulation of Thioamides

“…Likewise, the ester linked biologically relevant motifs 8g and 8n are also showing intense emission bands and could be useful as fluorescent drug carrier as well as fluorescent probe for cell imaging. 17 The enhanced fluorescence properties of-extended scaffolds 5oand 5q with longer life time 30 (3.42 ns for 5o; Scheme 3D) are notable and could be applicable for potential material applications. Ir).…”