TY - JOUR AU - Jin, Zexin; Teo, Yew Chin; Teat, Simon J.; Xia, Yan TI - Iterative Synthesis of Edge-Bent [3]Naphthylene SN - 0936-5214 SN - 1437-2096 PY - 2018 JO - Synlett JF - Synlett LA - EN VL - 29 IS - 19 SP - 2547 EP - 2551 ET - 2018/08/28 DA - 2018/11/21 KW - annulation KW - iterative synthesis KW - antiaromaticity KW - polycyclic conjugated hydrocarbons KW - [3]naphthylene AB - Polycyclic conjugated hydrocarbons (PCHs) containing antiaromatic rings are of fundamental and technical interest. [N]naphthylene is an intriguing family of PCHs consisting of alternatingly fused naphthalenoids and antiaromatic cyclobutadienoids (CBDs). We recently reported the first three regioisomers of the [N]naphthylene family, synthesized by catalytic arene-norbornene annulation (CANAL) reaction followed by acidic aromatization. We now report an iterative strategy for CANAL synthesis allowing us to synthesize the forth regioisomer, edge-bent [3]naphthylene. The optoelectronic properties, local paratropicity, and crystal packing of the edge-bent [3]naphthylene were studied and compared with its closely related regioisomer, center-bent [3]naphthylene. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1610261 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1610261 ER -