1 Tuning the Carbon Nanotube Selectivity – Optimizing Reduction Po- tentials and Distortion Angles in Perylenediimides Peter W. Münich, ‡,§ Christoph Schierl, ‡,§ Konstantin Dirian, § Michel Volland, § Stefan Bauroth, §,£ Leonie Wibmer, § Zois Syrgiannis, # Timothy Clark, £ Maurizio Prato, #,¶,† Dirk M. Guldi § § Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Uni- versität Erlangen-Nürnberg, 91058 Erlangen, Germany # Center of Excellence for Nanostructured Materials, Dipartimento di Scienze Chimiche e Farmaceutiche, INSTM unit of Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy £ Computer-Chemie-Centrum, Department of Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürn- berg, Nägelsbachstr. 25, 91052 Erlangen, Germany ¶ Carbon Nanobiotechnology Laboratory, CIC biomaGUNE, Paseo de Miramón 182, 20009 Donostia-San Sebastian (Spain) † Basque Fdn Sci, Ikerbasque, Bilbao 48013, Spain Experimental Section Synthetic procedures PDIs 1-3 were synthesized according to the procedure described in reference 15. Preparation of CoMoCAT-SWCNT hybrids For the creation of stable CoMoCAT-SWCNT hybrids, typically solid CoMoCAT-SWCNT were added to solutions of PDI derivatives 1-3 (5x10 -5 M) in D2O followed by several sonication and centrifugation (5kG) steps. Materials and methods Chemicals SDBS was purchased from Sigma-Aldrich and used without further purification. D2O was purchased from Deutero. CoMoCAT-SWCNT with a broad chirality range (0.7-0.9 nm in diameter, >77% of carbon as SWCNT) were purchased from Sigma Aldrich. Spectroscopy UV/Vis/nIR absorption measurements were performed using either a Perkin Elmer Lambda 2 spectrometer or a Cary 5000 spectrometer (Varian). Dependent on the optical density either 10x10mm or 10x2mm quarz cuvettes were used. NIR fluorescence measurements were done with a FluoroLog 3 spectrometer from HORIBA Yobin Yvon using a 450 W Xenon lamp and a Symphony InGaAs array in combination with an iHR320 imaging spectrometer. For emission spectroscopy in the visible range, a Fluoromax3 spectrometer from HORIBA Yobin Yvon was used. Femtosecond transient absorption measurements were performed with the transient absorption pump probe system HELIOS from Ultrafast Systems. To generate laser pulses with a pulse width of 150 fs and a wavelength of 387 nm a CPA-2110 titanium:sapphire laser system from Clark-MXR Inc was utilized. 387 nm excitation pulses were generated by second harmonic generation. All measurements were carried out in 2 mm OS quarz cuvettes.