Thiazolo[5,4-d]thiazoles – promising building blocks in the synthesis of semiconductors for plastic electronics

Abstract

The thiazolo [5,4-d]thiazole fused (bi)heterocycle is an electron deficient system with high oxidative stability and a rigid planar structure, enabling efficient intermolecular p-p overlap. The parent thiazolo [5,4d]thiazole moiety hence already possesses some appealing features towards applications in organic electronics. Moreover, aryl-functionalized thiazolo [5,4-d]thiazole derivatives -expanding the conjugated backbone of the semiconducting material -are easily prepared. Surprisingly, interest in thiazolo [5,4d]thiazole-based materials has been rather low, until quite recently, when the high potential of these molecules was widely recognized, notably in the field of organic photovoltaics. Despite the almost exponential growth of activity, the synthetic chemistry behind these molecules has only been explored to a minor extent and there is plenty of room for improvement and broadening of the material scope. In this review, an overview of the currently available synthetic methods and the range of materials prepared to date, together with their basic material properties and main applications, is provided, with the aim to facilitate and stimulate further progress in thiazolo [5,4-d]thiazole-based materials science.

Incorporating the Thiazolo[5,4-d]thiazole Unit into a Coordination Polymer with Interdigitated Structure

“…The heat of adsorption values were calculated using the ASAP 2020 v3.05 software. Water sorption isotherms were obtained volumetrically from a Quantachrome Autosorb iQ MP instrument molecules and polymers as well as their application in the field of organic electronics (e.g., OFETs, OSCs) [31,32]. In contrast, the tztz unit has been reported only in relatively few coordination compounds (15 hits in the CCDC database).…”

“…The tztz unit was incorporated into photoactive materials due to its rigid and planar structure and electron deficiency. Both Maes et al and Dessi et al reviewed the synthetic procedures to obtain tztz-containing small molecules and polymers as well as their application in the field of organic molecules and polymers as well as their application in the field of organic electronics (e.g., OFETs, OSCs) [31,32]. In contrast, the tztz unit has been reported only in relatively few coordination compounds (15 hits in the CCDC database).…”

Incorporating the Thiazolo[5,4-d]thiazole Unit into a Coordination Polymer with Interdigitated Structure

“…Both Maes et al and Dessi et al reviewed the synthetic procedures to obtain tztz-containing small molecules and polymers as well as their application in the field of organic electronics (e.g. OFETs, OSCs) [14,15]. In contrast, the tztz unit has been reported only in relatively few coordination compounds (15 hits in the CCDC database).…”

One-pot microwave-assisted synthesis of 2,5-bis(pyrazol-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazoles from pyrazole-4-carbaldehydes and dithiooxamide

“…Thiazolo [5,4-d]thiazoles represent an important class of bicyclic aromatic structures that have attractive properties for application in electronics, [1][2][3][4][5][6][7][8][9] optoelectronics, 10,11 and as ligands in coordination chemistry 10,12 etc. Many fused thiazoles are also biologically active and constitute an essential motif of pharmacologically active connections.…”

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AbstractAn efficient one-pot method for the synthesis of previously unknown of 2,5-bis(pyrazol-4-yl) [1,3]thiazolo [5,4-d]

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