▎ 摘　　要

NOVELTY - Manufacture of naphthyl silole compound (III) involves (i) reacting a brominated/iodinated biphenyl compound (I) with a lanthanoid-and-lithium-containing ate complex to obtain a lanthanoid complex, and (ii) reacting the lanthanoid complex with a silyl compound (II). USE - Manufacture of naphthyl silole compound used for preparing graphene nanoribbons (claimed) used for organic semiconductor, organic electroluminescent element, organic thin-film solar cell, luminescent material and electroconductive material. Can also be used for transparent electrode and high-speed transistor. ADVANTAGE - The method enables easy, economical and one-pot manufacture of naphthyl silole compound without using compound having very low flash point and boiling point or self-reactive organic peroxide. The graphene nanoribbons formed using the naphthyl silole compound has improved characteristics, such as electron/hole accepting ability, redox response, and charge transporting ability by precise control of band gap. DETAILED DESCRIPTION - Manufacture of naphthyl silole compound of formula (III) involves (i) reacting a brominated/iodinated biphenyl compound of formula (I) with a lanthanoid-and-lithium-containing ate complex to obtain a lanthanoid complex, and (ii) reacting the lanthanoid complex with a silyl compound of formula: R3aR3bSiCl2 (II). R1a,R1b = H, alkyl, cycloalkyl, (poly)ether, ester, halo, aryl, or heterocyclyl; or (R1a+R1b) = ring; R2 = aryl or heterocyclyl; R3a,R3b = 1-4C alkyl or phenyl;and X = bromo or iodo. INDEPENDENT CLAIMS are included for the following: (1) the compound (I); (2) naphthalen-2-yl sulfonate compound of formula (IV); (3) tricyclo(7.4.0.02,6)trideca-1(13),2(6),7,9,11-pentaene compound of formula (IIIa); and (4) graphene nanoribbons, which comprise hexacyclo(12.12.0.02,11.03,8.015,20.021,26)hexacosa-1(14),2(11),3(8),4,6,9,12,15(20),16,18,21(26),22,24-tridecaene structural unit(s) of formula (A1). R4 = 1-4C alkyl, 1-4C haloalkyl, or aryl; n = 0 or more;and R2a = heteroaryl.