A simple one‐pot synthesis of [1]benzotelluro[3,2‐b][1]‐benzotellurophenes and its selenium and sulfur analogues from 2,2′‐dibromodiphenylacetylene

Abstract

Treatment of 2, 2′‐dibromodiphenylacetylene 7 with tert‐butyllithium followed by tellurium insertion resulted in intramolecular ring closure to afford [1]benzotelluro[3,2‐b][1]benzotellurophene 8a. Similarly, [1]benzoseleno‐[3,2‐b][1]benzoselenophene 8b and [1]benzothieno[3,2‐b][1]benzothiophene 8c were also obtained.

Thienoacene‐Based Organic Semiconductors

“…On the other hand, elegant and high-yield syntheses of BTBT and its selenium and tellurium analogues from di( o -bromophenyl)acetylene were developed by Sashida and Yasuike (route d). [ 95 ] The parent BTBT can be functionalized at the 2-and 7-positions selectively via aromatic electrophilic substitution reactions; one representative example is the Friedel-Crafts acylation followed by the Wolff-Kishner reduction to give dialkyl-BTBTs ( 33c ), [ 86 ] which are very important materials that yield highperformance OTFTs by solution processes. Another important BTBT intermediate is 2,7-diiodo-BTBT, which can be conveniently synthesized from commercially available disodium 4,4´-dinitrostilbene-2,2´-disulfonate.…”

Phosphonium‐ and Borate‐Bridged Zwitterionic Ladder Stilbene and Its Extended Analogues

“…Furthermore, their electronic structures can be modulated by the incorporation of appropriate bridging moieties. A number of fascinating ladder systems embedding various elements, such as Group 13 boron, [2] Group 14 silicon, [3] Group 15 nitrogen [4] and phosphorus, [5] and Group 16 sulfur and selenium, [6,7] as the bridging moiety have been reported. We have also synthesized a series of ladder stilbenes and their extended analogues containing main-group elements and have demonstrated that their properties are highly dependent on the nature of the elements.…”

Ladder π‐Conjugated Materials Containing Main‐Group Elements

“…[44] In contrast to the carbonbridged system, significant progress has recently been made in the chemistry of the main-group element-bridged LOPVs. A number of bridged stilbenes and more extended OPV derivatives embedded with various elements, such as Group 14 Si, [45][46][47][48][49] Group 15 N [50][51] and P, [52,53] and Group 16 S and Se, [48,50,[54][55][56] as the bridging elements, have been reported to date. Their inherent characteristics in terms of the electronic structures are highly dependent on the incorporated main-group elements.…”

“…Replacement of the benzene rings in the PAHs with thiophene rings would be a promising strategy to increase the diversity of the modification of the molecular and electronic structures, which may lead to the development of more superb organic semiconductors. Various thiophene analogues of PAHs comprising interesting molecular structures, such as linear acene‐type molecules 30 ,36–38, 54–56, 71, 72 helicene‐type derivatives 31 ,73 and cyclic fused oligothiophene 32 ,74 have been reported to date (Scheme ).…”