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A Donor–Acceptor–Donor Structured Organic Conductor with S···S Chalcogen Bonding
Bai, Monalisa,Thomas, Sajesh P.,Kottokkaran, Ranjith,Nayak, Susanta K.,Ramamurthy, Praveen C.,Guru Row, T. N. American Chemical Society 2014 Crystal Growth & Design Vol.14 No.2
<P>A novel thiophene derivative 7,9-di(thiophen-2-yl)-8<I>H</I>-cyclopenta[a]acenaphthylen-8-one (DTCPA) is shown to exhibit high electrical conductivity (1.97 × 10<SUP>–2</SUP> ± 0.0018 S/cm at RT) in the crystalline state. The material shows two orders of increase in conductivity from normal solid to single crystalline state. The crystal structure has S···S chalcogen bonding, C–H···O hydrogen bonding, and π···π stacking as the major intermolecular interactions. The nature and strength of the S···S interactions in this structure have been evaluated by theoretical charge density analysis, and its contribution to the crystal packing quantified by Hirshfeld surface analysis. Further, thermal and morphological characterizations have been carried out, and the second harmonic generation (SHG) efficiency has been measured using the Kurtz–Perry method.</P><P>A novel donor−acceptor−donor structured material with S···S chalcogen bonding is shown to exhibit high electrical conductivity in the crystalline state. Two different types of intermolecular S···S interactions present in the material are shown to be similar to type I and type II halogen bonds, in terms of charge density distribution.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/cgdefu/2014/cgdefu.2014.14.issue-2/cg401069y/production/images/medium/cg-2013-01069y_0014.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cg401069y'>ACS Electronic Supporting Info</A></P>