Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

• Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

• , new OFET-based acid vapor sensors were developed from 150 by synergistically utilizing its charge transport and protonation−deprotonation properties. The solution-phase synthesis of a non-benzenoid nanoribbon from an azulene-containing polymer via alkyne benzannulation was reported by Morin and co

• -workers (Scheme 20) [98]. The starting polymer 152 was synthesized using Suzuki cross coupling and is regiorandom, meaning the orientation of the azulene units within the main chain is not defined. Polymer 152 was annulated using MsOH (methanesulfonic acid) yielding the non-alternant graphene nanoribbon

• 153. The nanoribbon is soluble in common organic solvents and exhibits conductivity values up to 1.5∙10−3 S∙cm−1 when doped by TFA in the thin film state. The serendipitous synthesis of azulene-embedded [5]helicenes was reported by Usui, Suemune, and co-workers [99]. The unexpected formation of an

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• ]. When three HBCs were fused together linearly, the graphene nanoribbons would be constructed. Wang [46] and Campaña [52] groups separately reported the synthesis of graphene nanoribbon 73 (Scheme 8), which contains four [5]carbohelicenes due to bulky tert-butyl groups as lateral chains. In brief

• (M)-110 at 684 nm were up to 4.50 × 10−2 and 4.22 × 10−2, respectively. Wang and co-workers reported a chiral graphene nanoribbon 115 (Scheme 12) by linearly fusing four HBS units in a helical manner [46]. The synthesis started by construction of a HBC-dimer 111. para-Iodization of 111 gave compound

• 112 in a 91% yield. Scholl oxidation of 112, and then Sonogashira coupling of 113 yielded the bisalkyne, which was ready for a second Diels−Alder reaction to give precursor 114. Through dehydrocyclization induced by DDQ and TfOH, precursor 114 was transformed to nanoribbon 115 in a 5% yield. This

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T1 and T2 films was tested by a four-probe method. Keywords: hydrogen bond; nanoribbon; self-assembly; tetrathiafulvalene; urethane; Introduction