Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2009 Nanophase segregated mesophase morphology in self-organized novel disc-rod oligomesogens Hari Krishna Bisoyi, V. A. Raghunathan and Sandeep Kumar* Raman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, India. Electronic supplementary information Synthesis of novel disc-rod oligomers The synthesis of disc-rod oligomesogens is outlined in Scheme 1. Compounds 1-5 and ω-bromo alkoxycyanobiphenyls (RBr) were prepared as reported. Powdered KOH (135 mg, 2.4 mmol) was mixed with DMSO (10 ml) at room temperature and stirred for 10 min. Hexaacetoxy-TCQ (66.8 mg, 0.1 mmol) followed by the appropriate ω-bromo alkoxycyanobiphenyl (2.4 mmol) was added and the reaction mixture was stirred at 55 o C for 24 h and then worked up by addition of ice-water and extracted with dichloromethane. The crude product was purified by column chromatography (silica gel, hexane-ethyl acetate 1:1 followed by dichloromethane) and then crystallized from acetone or precipitated with dichloromethane-ethyl acetate to afford pure yellow material in about 40% yield. 6a: 1H NMR (400 MHz; CDCl 3 ; Me 4 Si) δ H 7.71 (s, 3H, Ar-H from TCQ), 7.65 (d, 12H, J = 6.5 Hz, Ar-H from biphenyl), 7.59 (d,12H, J = 6.5 Hz, Ar-H from biphenyl), 7.49 (d, 12H, J = 8.8 Hz, Ar-H from biphenyl), 6.96 (d, 12H, J = 8.9 Hz, Ar-H from biphenyl), 6.90 (s, 3H, Ar-H from TCQ), 4.2-4.1 (m, 12H, Ar-OCH 2 ), 3.98-4.05 (m, 12H, Ar-OCH 2 ), 2.0-1.91 (m, 12H, CH 2 ), 1.89-1.82 (m, 12H, CH 2 ), 1.65-1.60 (m, 24H, CH 2 ). All other compounds give similar spectra except for more number of aliphatic methylene protons.