Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• Abstract The polycyclic skeleton of tris(4,5-dehydro-2,3:6,7-dibenzotropone) is a key structural fragment in carbon schwarzites, a theoretical form of negatively curved carbon allotrope. This report presents a new synthesis of this compound using a Ni-mediated Yamamoto coupling reaction and structural

• , expanding its π-skeleton through the Barton–Kellogg and Scholl reactions led to the successful synthesis of a curved polycyclic arene containing three heptagons and two pentagons. Keywords: carbon schwarzites; polycyclic arenes; Scholl reaction; seven-membered carbocycle; Yamamoto coupling; Introduction

• synthesis of 1 using a Ni-mediated Yamamoto coupling reaction and the simultaneous crystallization of its two different conformers from the same solution. Expanding the π-skeleton of 1 through a Barton–Kellogg reaction followed by a subsequent Scholl reaction resulted in a new polycyclic arene (3 in Figure

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• monomer are required. Both chemical [43] and electrochemical polymerisation [44] have been used to incorporate a TTF moiety within the polythiophene backbone. Yamamoto coupling of diiodo monomers 1a and 1b provided polymer 1c, albeit with a modest molecular weight (Mw = 5800 Da) compared to that of the

• method of purification and to narrow their polydispersity. Using Yamamoto coupling compound 14b was polymerised. Use of DMF alone as solvent led to a polymer that was sparingly soluble in CH2Cl2 [77]. However, a mixture of DMF:toluene (1:1) as a medium for Yamamoto polymerisation afforded polymer 35 as a

• afforded iodoterthiophene 52 in a 74% yield. Compound 52 was used to explore other possibilities for synthesising sexithiophene 51, including Ullmann and Yamamoto coupling, which provided 51 in 43 and 10% yield, respectively. Sexithiophene 51 exhibited a strong propensity to aggregate even in chloroform

Chiroptical properties of 1,3-diphenylallene-anchored tetrathiafulvalene and its polymer synthesis

• Masashi Hasegawa,
• Junta Endo,
• Seiya Iwata,
• Toshiaki Shimasaki and
• Yasuhiro Mazaki

Beilstein J. Org. Chem. 2015, 11, 972–979, doi:10.3762/bjoc.11.109

• . Previously, a racemic conjugated polymer in the literature was prepared by a Suzuki–Miyaura or Yamamoto coupling reaction from (rac)-8 [17]. In contrast, to the best of our knowledge, there is no example of a chiral polymer based on the 1,3-diphenylallene frameworks that can be a unit of copolymer with

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• polycondensation reactions such as Suzuki [17], Stille [18] and Heck [19] coupling are especially useful. Other suitable reactions are Ni-mediated Yamamoto coupling [20], Sonogashira coupling [21], or electrochemical polymerization [22]. In the following, a brief review of recently prepared DPP based polymers is

• )DPP] by Yamamoto coupling of a dibrominated thiophenylDPP derivative such as M-3. An ambipolar near-infrared light-emitting transistor (LET) could be prepared from this material which exhibited hole and electron mobilities of 0.1 cm2 V−1 s−1 and up to 0.09 cm2 V−1 s−1, respectively. These values were