S-5
 
 O=C(N(C(CC)CC)C7=O)C2=CC=C(C4=CC=C6C5=C(C(N(C(CC)CC)C6=O)=O)C=CC3=C45)C1=C3C=CC7=C12

N,N‘-Bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide); 2,9-bis-(1-ethylpropyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone; 2,9-bis-(3-pentyl)anthra[2,1,9-def;6,5,10-d‘e‘f‘]diisoquinoline-1,3,8,10(2H,9H)-tetraone, RN 110590-81-3:
M.p. >360°C, red crystals. UV (CHCl3): λmax (ε) = 457.5 nm (17910), 488 (50120), 524 (83560). C34H30N2O4 (530.6) calcd. C 76.96, H 5.70, N 5.28; found C 77.19, H 5.70, N 5.37.


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112. Mizoshita, N.; Yamanaka, K.; Hiroto, S.; Shinokubo, H.; Tani, T.; Inagaki, S- ‘Energy and electron transfer from fluorescent mesostructured organosilica framework to guest dyes’, Langmuir 2012, 28, 3987-3994.

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120. Moreno-Lopez, J. C.; Grizzi, O.; Martiarena, M. L.; Sanchez, E. A. ‘Initial growth of N,N'-bis(1-ethylpropyl) perylene-3,4,9,10-tetracarboxdiimide films on Cu(100)’, J. Phys. Chem. C 2013, 117, 11679-11685.

121. Edri, E.; Kirmayer, S.; Cahen, D.; Hodes, G- ‘High open-circuit voltage solar cells based on organic-inorganic lead bromide perovskite’, J. Phys. Chem. Lett. 2013, 4, 897-902.

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123. Ye, T.; Singh, R.; Butt, H.-J.; Floudas, G.; Keivanidis, P. E.‘Effect of local and global structural order on the performance of perylene diimide excimeric solar cells’, ACS Appl. Materials & Interfaces 2013, 5, 11844-11857.

124. Zhang, Xinping; Dou, Fei; Liu, Hongmei ‘Charge-transfer complex coupled between polymer and H-aggregate molecular crystals’, J. Polymer Science, Part B: Polymer Physics 2013, 51, 749-755.

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126. Wei, Huimin; Zhao, Nan; Jiang, Nan; Duan, Wenfeng; Gao, Baoxiang ‘The synthesis and electro-optical properties of perylene dicarboximide dimer with electron withdrawing groups’, Advanced Materials Research (Durnten-Zurich, Switzerland) 2014, 936(Material Science and Engineering Technology, 950-954.

127. Sharenko, A.; Gehrig, D.; Laquai, F.; Nguyen, T.-Q. ‘The effect of solvent additive on the charge generation and photovoltaic performance of a solution-processed small molecule: Perylene diimide bulk heterojunction solar cell’, Chemistry of Materials 2014, 26, 4109-4118.

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129. Ghosh, I.; Ghosh, T.; Bardagi, J. I.; Koenig, B. ‘Reduction of aryl halides by consecutive visible light-induced electron transfer processes’, Science (Washington, DC, United States) 2014, 346, 725-728.

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131. Miyake, G. M.; Theriot, J. C.‘Perylene as an organic photocatalyst for the radical polymerization of functionalized vinyl monomers through oxidative quenching with alkyl bromides and visible light’, Macromolecules (Washington, DC, United States) 2014, 47, 8255-8261.

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134. Schwarz, C.; Milan, F.; Hahn, T.; Reichenberger, M.; Kuemmel, S.; Koehler, A. ‘Ground state bleaching at donor-acceptor interfaces’, Adv. Functional Materials 2014, 24, 6439-6448.

135. Singh, R.; Aluicio-Sarduy, E.; Kan, Z.; Ye, T.; MacKenzie, R. C. I.; Keivanidis, P. E. ‘Fullerene-free organic solar cells with an efficiency of 3.7% based on a low-cost geometrically planar perylene diimide monomer’, J. Materials Chemistry A: Materials for Energy and Sustainability 2014, 2, 14348-14353.

136. Gehrig, D. W.; Roland, S.; Howard, I. A.; Kamm, V.; Mangold, H.; Neher, D.; Laquai, F. ‘Efficiency-limiting processes in low-bandgap polymer: Perylene diimide photovoltaic blends’, J. Phys. Chem. C 2014, 118, 20077-20085.

137. Li, Mingguang; Wang, Lei; Liu, Jiangang; Zhou, Ke; Yu, Xinhong; Xing, Rubo; Geng, Yanhou; Han, Yanchun ‘Cooperative effects of solvent and polymer acceptor co-additives in P3HT:PDI solar cells: simultaneous optimization in lateral and vertical phase separation’, PhysChemChemPhys 2014, 16, 4528-4537.

138. Dobruchowska, E.; Marszalek, T.; Ulanski, J. ‘Anisotropic perylenediimide/polycarbonate composites produced by a single batch solution based method’, Thin Solid Films 2014, 564, 361-366.

139. Li, Mingguang; Liu, Jiangang; Cao, Xinxiu; Zhou, Ke; Zhao, Qiaoqiao; Yu, Xinhong; Xing, Rubo; Han, Yanchun ‘Achieving balanced intermixed and pure crystalline phases in PDI-based non-fullerene organic solar cells via selective solvent additives’, PhysChemChemPhys 2014, 16, 26917-26928.

140. Handa, N. V.; Shirtcliff, L. D.; Lavine, B. K.; Powell, D. R.; Berlin, D. K. ‘1,6- and 1,7-regioisomers of perylene tetracarboxylic dianhydride and diimide: The effects of neutral bay substituents on the electrochemical and structural properties’, Phosphorus, Sulfur and Silicon and the Related Elements 2014, 189, 738-752.

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142. Rybtchinski, B.; Krieg, E. M.; Weissman, H.; Albeck, S.; Tldhar, Y.; Cohen, E. ‘Separation of nanoparticles using self-assembled perylene diimide membranes’, U.S. Pat. Appl. Publ. 2015, US 20150375180 A1 20151231.

143. Yu, Zhenyi; Wu, Yishi; Liao, Qing; Zhang, Haihua; Bai, Shuming; Li, Hui; Xu, Zhenzhen; Sun, Chunlin; Wang, Xuedong; Yao, Jiannian; et al. ‘Self-assembled microdisk lasers of perylenediimides’, J. Am. Chem. Soc. 2015, 137, 15105-15111.

144. Hendsbee, A. D.; McAfee, S. M.; Sun, J.-P.; McCormick, T. M.; Hill, I. G.; Welch, G. C. ‘Phthalimide-based π-conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells’, J. Materials Chemistry C: Materials for Optical and Electronic Devices 2015, 3, 8904-8915.

145. Shoer, L. E.; Eaton, S. W.; Margulies, E. A.; Wasielewski, M. R. ‘Photoinduced electron transfer in 2,5,8,11-tetrakis-donor-substituted perylene-3,4:9,10-bis(dicarboximides) ’, J. Phys. Chem. B 2015, 119, 7635-7643.

146. Yang, Yang; Li, Gang ‘Multiple donor/acceptor bulk heterojunction solar cells’, PCT Int. Appl. 2015, WO 2015042609 A1 20150326.

147. Chen, Yuxia; Zhang, Xin; Zhan, Chuanlang; Yao, Jiannian ‘In-depth understanding of photocurrent enhancement in solution-processed small-molecule:perylene diimide non-fullerene organic solar cells’, Physica Status Solidi A: Applications and Materials Science 2015, 212, 1961-1968.

148. Chen, H.-C.; Hsu, C.-P.; Reek, J. N. H.; Williams, R. M.; Brouwer, A. M. ‘Highly soluble benzo[ghi] perylenetriimide derivatives: Stable and air-insensitive electron acceptors for artificial photosynthesis’, ChemSusChem 2015, 8, 3639-3650.

149. Liu, Xiujie; Zhang, Qi; Meng, Xiangtai ‘Gold-substituted perylene diimide derivative at bay site’, Faming Zhuanli Shenqing 2015, CN 104262396 A 20150107.

150. Aluicio-Sarduy, E.; Singh, R.; Kan, Z.; Ye, T.; Baidak, A.; Calloni, A.; Berti, G.; Duo, L.; Iosifidis, A.; Beaupre, S.; et al. ‘Elucidating the impact of molecular packing and device architecture on the performance of nanostructured perylene diimide solar cells’, ACS Applied Materials & Interfaces 2015, 7, 8687-8698.

151. Su, Yajun; Li, Yan; Liu, Jiangang; Xing, Rubo; Han, Yanchun ‘Donor-acceptor cocrystal based on hexakis(alkoxy)triphenylene and perylenediimide derivatives with an ambipolar transporting property’, Nanoscale 2015, 7, 1944-1955.

152. Singh, R.; Shivanna, R.; Iosifidis, A.; Butt, H.-J.; Floudas, G.; Narayan, K. S.; Keivanidis, P. E. ‘Charge versus energy transfer effects in high-performance perylene diimide photovoltaic blend films’, ACS Applied Materials & Interfaces 2015, 7, 24876-24886.

153. Moreno-Lopez, J. C.; Grizzi, O.; Sanchez, E. A.‘Thermal Ssability of N,N'-bis(1-ethylpropyl)perylene-3,4,9,10-tetracarboxdiimide films on Cu(100)’, J. Phys. Chem. C 2016, 120, 19630-19635.

154. Weintraub, M. T.; Xhakaj, E.; Austin, A.; Szarko, J. M. ‘The effects of donor : acceptor intermolecular mixing and acceptor crystallization on the composition ratio of blended, spin coated organic thin films’, J. Materials Chemistry C: Materials for Optical and Electronic Devices 2016, 4, 7756-7765.

155. Hendsbee, A. D.; Sun, J.-P.; Law, W. K.; Yan, H.; Hill, I. G.; Spasyuk, D. M.; Welch, G. C.‘Synthesis, self-assembly, and solar cell performance of N-annulated perylene diimide non-fullerene acceptors’, Chemistry of Materials 2016, 28, 7098-7109.

156. Wang, Jialin; Liang, Ziqi ‘Synergetic solvent engineering of film nanomorphology to enhance planar perylene diimide-based organic photovoltaics’, ACS Appl. Materials & Interfaces 2016, 8, 22418-22424.

157. Lindquist, R. J.; Phelan, B. T.; Reynal, A.; Margulies, E. A.; Shoer, L. E.; Durrant, J. R.; Wasielewski, M. R. ‘Strongly oxidizing perylene-3,4-dicarboximides for use in water oxidation photoelectrochemical cells’, J. Materials Chemistry A: Materials for Energy and Sustainability 2016, 4, 2880-2893.

158. Yu, Zhenyi; Wu, Yishi; Zhang, Haihua; Wang, Xuedong; Chen, Jianwei; Yao, Jiannian; Fu, Hongbing ‘Self-assembled 1D-nanowire lasers of perylenediimides’, ChemPhysChem 2016, 17, 3160-3164.

159. Chen, H.-C.; Williams, R. M.; Reek, J. N. H.; Brouwer, A. M. ‘Robust benzo[ghi]perylenetriimide dye-sensitized electrodes in air-saturated aqueous buffer solution’, Chem. Europ. J. 2016, 22, 5489-5493.

160. Yu, Zhenyi; Wu, Yi-Shi; Chen, Jianwei; Sun, Chunlin; Fu, Hongbing ‘ortho-Heterofluorene perylenediimides: synthesis, photophysical and exciton dynamic properties’, PhysChemChemPhys 2016, 18, 32678-32681.

161. Hanson, K.; Hill, S.; Dilbeck, T. ‘Molecular photon upconversion using organic-inorganic hybrid interfaces’, PCT Int. Appl. 2016, WO 2016039976 A1 20160317.

162. Zhu, Xinhai; Sun, Guoquan; Ren, Shuya; Wan, Yiqian; Huang, Manna ‘Method for indirect electrocatalytic synthesis of 2-arylpyrrole compounds’, Faming Zhuanli Shenqing 2016, CN 105568312 A 20160511.

163. Yang, Xiao-Yu; Xu, Wei-Long; Zheng, Fei; Liu, Jian-Qiang; Hao, Xiao-Tao ‘Impact of solvent additive on exciton dissociation in P3HT : EP-PDI blend film via controlling morphology’, Journal of Physics D: Applied Physics 2016, 49, 255502/1-255502/8.

164. Zhang, Hao; Tao, Kai; Liu, Di; Wu, Kui; Wang, Fuyi; Yang, Jingfa; Zhao, Jiang ‘Examining dynamics in a polymer matrix by single molecule fluorescence probes of different sizes’, Soft Matter 2016, 12(35, 7299-7306.

165. Yang, W.; Zhao, J.; Sonn, C.; Escudero, D.; Karatay, A.; Yaglioglu, H. G.; Kucukoz, B.; Hayvali, M.; Li, C.; Jacquemin, D. ‘Efficient intersystem crossing in heavy-atom-free perylenebisimide derivatives’, J. Phys. Chem. C 2016, 120, 10162-10175.

166. Kang, H.; Si, Y.; Liu, J.; Chen, L.; Li, Y.; Chen, H.; Groeper, J.; Yang, B. ‘An experimental and theoretical study of dimethylaminostyryl BODIPY-perylenetetracarboxylic derivative dyads: Synthesis, properties and DFT calculation’, RSC Advances 2016, 6, 23094-23101.

167. Viswanath, L. C. Kasi; Bernhardt, J.; Kumar Gnanasekaran, K.; Want, C.; Frank, J.; Faulkner, J.; Krishnan, S. ‘Alkyl- and aryl-substituted benzo[ghi]perylenetriimides: Synthesis, characterization and comparison of electrochemical and spectroscopic properties’, Dyes and Pigm. 2016, 134, 453-458.

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169. Li, Mingguang; Liang, Qiuju; Zhao, Qiaoqiao; Zhou, Ke; Yu, Xinhong; Xie, Zhiyuan; Liu, Jiangang; Han, Yanchun ‘A bi-continuous network structure of p-DTS(FBTTh2)2/EP-PDI via selective solvent vapor annealing’, J. Materials Chemistry C: Materials for Optical and Electronic Devices 2016, 4, 10095-10104.

170. Liu, N.-W.; Liang, S.; Manolikakes, G. ‘Visible-light photoredox-catalyzed aminosulfonylation of diaryliodonium salts with sulfur dioxide and hydrazines’, Adv. Synthesis & Catalysis 2017, 359, 1308-1319.

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172. Cohen, E.; Weissman, H.; Shimoni, E.; Kaplan-Ashiri, I.; Werle, K.; Wohlleben, W.; Rybtchinski, B. ‘Robust aqua material: A pressure-resistant self-assembled membrane for water purification’, Angew. Chem., Int. Ed. 2017, 56, 2203-2207.

173. Zhang, Hao; Li, Desheng; Wu, Kui; Wang, Fuyi; Yang, Jingfa; Zhao, Jiang ‘Retarded local dynamics of single fluorescent probes in polymeric glass due to interaction strengthening’, Polymer 2017, 116, 452-457.

174. Dominguez, C.; Baena, M. J.; Coco, S.; Espinet, P. ‘Perylenecarboxydiimide-gold(I) organometallic dyes. Optical properties and Langmuir films’, Dyes and Pigm. 2017, 140, 375-383.

175. Rybtchinski, B.; Cohen, E.; Weissman, H. ‘Perylene diimide based membrane and methods of use thereof in filtration system’, PCT Int. Appl. 2017, WO 2017006325 A1 20170112.

176. Solak, S.; Ricciardulli, A. G.; Lenz, T.; Craciun, N. I.; Blom, P. W. M.; Wetzelaer, G. A. H. ‘Open-circuit voltage loss in annealed P3HT:perylene diimide bulk heterojunction solar cells’, Appl. Phys. Lett. 2017, 110, 163301/1-163301/4.

177. Wang, Helin; Chen, Lingcheng; Xiao, Yi ‘Heterologous perylene diimide arrays: Potential non-fullerene acceptors in organic solar cells’, J. Materials Chemistry C: Materials for Optical and Electronic Devices 2017, 5, 8875-8882.

178. Signoretto, M.; Zink-Lorre, N.; Suarez, I.; Font-Sanchis, E.; Sastre-Santos, A.; Chirvony, V. S.; Fernandez-Lazaro, F.; Martinez-Pastor, J. P. ‘Efficient optical amplification in a sandwich-type active-passive polymer waveguide containing perylenediimides’, ACS Photonics 2017, 4, 114-120.

179. Wang, Jialin; Peng, Jiajun; Liu, Xiaoyu; Liang, Ziqi ‘Efficient and stable ternary organic solar cells based on two planar nonfullerene acceptors with tunable crystallinity and phase miscibility’, ACS Appl. Materials & Interfaces 2017, 9, 20704-20710.

180. Wu, Jiajun; He, Dezhi; Zhang, Li; Liu, Yudong; Mo, Xiaogang; Lin, Jianbin; Zhang, Hui-jun ‘Direct synthesis of large-scale ortho-iodinated perylene diimides: Key precursors for functional dyes’, Organic Lett. 2017, 19, 5438-5441.

181. Wang, Helin; Chen, Lingcheng; Zhao, Zhenbo; Xiao, Yi ‘Aryl-bisalkynyl bridged perylene diimides dimers: Efficient synthesis, properties and improved electron mobilities’, Dyes and Pigm. 2017, 144, 184-189.

182. Tose, L. V.; Murgu, M.; Vaz, B. G.; Romao, W. ‘Application of atmospheric solids analysis probe mass spectrometry (ASAP-MS) in petroleomics: Analysis of condensed aromatics standards, crude oil, and paraffinic fraction’, J. Am. Soc. Mass Spectrometry 2017, DOI:10.1007/s13361-017-17.

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