S1 Supporting Information for: Perpendicular Organization of Macromolecules: Synthesis and Alignment Studies of a Soluble Poly(iptycene) Samuel W. Thomas III 1 , Timothy M. Long 1 , Brian D. Pate 2,3 , Steven R. Kline 4 , Edwin L. Thomas 2,3 and Timothy M. Swager* 1,3 Department of Chemistry 1 , Department of Materials Science and Engineering 2 and Institute for Soldier Nanotechnologies 3 , Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139; NIST Center for Neutron Research 4 , Gaithersburg, Maryland 20899. Experimental Section General. 1 H NMR spectra for all compounds were recorded on a Varian MERCURY (300Mhz) instrument, using deuterochloroform as a reference or internal deuterium lock. The chemical shift data for each signal are given in units of δ (ppm) relative to tetramethylsilane (TMS) where δ(TMS) = 0, and referenced to the solvent residual. 13 C NMR spectra were recorded on a Varian MERCURY (75MHz) instrument using internal deuterium lock and proton decoupling. High resolution mass spectra (HRMS) were obtained on a Finnigan MAT 8200 system using sector double focus and an electron impact source with an ionizing voltage of 70 V, and with a Bruker DALTONICS APEX II, 3 Tesla, FT-ICR-MS with ESI source or EI/CI source. Ultraviolet-visible absorption spectra were measured with a Cary 50 UV/Visible spectrometer. Polarized fluorescence spectra were measured with a SPEX Fluorolog-τ3 fluorimeter (model FL312, 450W xenon lamp) equipped with a 1935B polarization kit. Polymer molecular weights were determined by Gel Permeation Chromatography (GPC) running with tetrahydrofuran as the eluent versus polystyrene standards (PolySciences). A Hewlett Packard series 1100 HPLC instrument equipped with a Plgel 5mm Mixed-C (300 x 7.5 mm) column was used. Preparative-scale GPC was performed using THF as the eluent with a Rainin HPLC instrument equipped with an isocratic solvent pump and UV/Vis detector and a preparative-scale Plgel column. All synthetic manipulations were performed under an argon atmosphere using standard Schlenk techniques unless otherwise indicated. Solvents were purified and dried by standard techniques. 1 N-bromosuccinimide (NBS) was purified by recrystallization from hot water. All other chemicals were of reagent grade and used without further purification. 1,4-dimethoxyanthracene 2 and 7,16-(2’,3’-anthraceno)-7,16- dihydroheptacene 3 were prepared according to literature procedures. Scheme S-1