M. Kardos and D. E. German-patent, , 1913.

H. Langhals, Cyclic carboxylic imide structures as structure elements of high stability. Novel developments in perylene dye chemistry, Heterocycles, vol.40, pp.477-500, 1995.

H. C. Zollinger and . Chemistry, , 2003.

W. Herbst and K. Hunger, Industrial Organic Pigments: Production, Properties, Applications, 2004.

R. Loutfy, A. Hor, P. Kazmaier, and M. Tam, Layered organic photoconductive (OPC) devices incorporating N, N'-disubstituted diimide and bisarylimidazole derivatives of perylene-3,4,9,10-tetracarboxylic acid, J. Imaging Sci, vol.33, pp.151-159, 1989.

N. Soh and T. Ueda, Perylene bisimide as a versatile fluorescent tool for environmental and biological analysis: A review, Talanta, vol.85, pp.1233-1237, 2011.

H. Quante, Y. Geerts, and K. Müllen, Synthesis of Soluble Perylenebisamidine Derivatives. Novel Long-Wavelength Absorbing and Fluorescent Dyes, Chem. Mater, vol.9, pp.495-500, 1997.

R. S. Sánchez, R. Gras-charles, J. L. Bourdelande, G. Guirado, and J. Hernando, Light-and Redox-Controlled Fluorescent Switch Based on a Perylenediimide-Dithienylethene Dyad, J. Phys. Chem. C, vol.116, pp.7164-7172, 2012.

Z. Yu, Y. Wu, Q. Liao, H. Zhang, S. Bai et al., Self-Assembled Microdisk Lasers of Perylenediimides, J. Am. Chem. Soc, vol.137, pp.15105-15111, 2015.

J. E. Anthony, Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics, Chem. Mater, vol.23, pp.583-590, 2011.

C. Li and H. Wonneberger, Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow, Adv. Mat, vol.24, pp.613-636, 2012.

E. Kozma and M. Catellani, Perylene diimides based materials for organic solar cells, Dyes Pigm, vol.98, pp.160-179, 2013.

F. Fernández-lázaro and N. Zink-lorre, Sastre-Santos, Á. Perylenediimides as non-fullerene acceptors in bulk-heterojunction solar cells (BHJSCs), J. Mater. Chem. A, vol.4, pp.9336-9346, 2016.

M. R. Wasielewski, Self-Assembly Strategies for Integrating Light Harvesting and Charge Separation in Artificial Photosynthetic Systems, Acc. Chem. Res, vol.42, 1910.

M. P. O'neil, M. P. Niemczyk, W. A. Svec, D. Gosztola, G. L. Gaines et al., Picosecond optical switching based on biphotonic excitation of an electron donor-acceptor-donor molecule, Science, vol.257, pp.63-65, 1992.

S. Prathapan, S. I. Yang, J. Seth, M. A. Miller, D. F. Bocian et al., Synthesis and Excited-State Photodynamics of Perylene-Porphyrin Dyads. 1. Parallel Energy and Charge Transfer via a Diphenylethyne Linker, J. Phys. Chem. B, vol.105, pp.8237-8248, 2001.

J. M. Serin, D. W. Brousmiche, and J. M. Fréchet, Cascade energy transfer in a conformationally mobile multichromophoric dendrimer, Chem. Commun, pp.2605-2607, 2002.

S. Fukuzumi, K. Ohkubo, J. Ortiz, A. M. Gutierrez, F. Fernandez-lazaro et al., Formation of a long-lived charge-separated state of a zinc phthalocyanine-perylenediimide dyad by complexation with magnesium ion, Chem. Commun, pp.3814-3816, 2005.

Z. An, S. A. Odom, R. F. Kelley, C. Huang, X. Zhang et al., Synthesis and Photophysical Properties of Donor-and Acceptor-Substituted 1,7-Bis(arylalkynyl)perylene-3,4:9,10-bis(dicarboximide)s, J. Phys. Chem. A, vol.113, pp.5585-5593, 2009.

S. Shoaee, Z. An, X. Zhang, S. Barlow, S. R. Marder et al., Charge photogeneration in polythiophene-perylene diimide blend films, Chem. Commun, pp.5445-5447, 2009.

L. Rocard, A. Berezin, F. De-leo, and D. Bonifazi, Templated Chromophore Assembly by Dynamic Covalent Bonds, Angew. Chem. Int. Ed, vol.54, pp.15739-15743, 2015.

L. Rocard, D. Wragg, S. A. Jobbins, L. Luciani, J. Wouters et al., Templated Chromophore Assembly on Peptide Scaffolds: A Structural Evolution, Chem. Eur. J, vol.24, pp.16136-16148, 2018.

F. Yukruk, A. L. Dogan, H. Canpinar, D. Guc, and E. U. Akkaya, Water-Soluble Green Perylenediimide (PDI) Dyes as Potential Sensitizers for Photodynamic Therapy, Org. Lett, vol.7, pp.2885-2887, 2005.

M. Sun, K. Müllen, and M. Yin, Water-soluble perylenediimides: Design concepts and biological applications, Chem. Soc. Rev, vol.45, pp.1513-1528, 2016.

J. Roncali, Synthetic principles for bandgap control in linear ?-conjugated systems, Chem. Rev, vol.97, pp.173-205, 1997.

J. Roncali, Molecular Engineering of the Band Gap of ?-Conjugated Systems: Facing Technological Applications, Macromol. Rapid Commun, vol.28, pp.1761-1775, 2007.

T. Mileti?, A. Fermi, I. Orfanos, A. Avramopoulos, F. De-leo et al., Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons, Chem. Eur. J, vol.23, pp.2363-2378, 2017.

C. Huang, S. Barlow, and S. R. Marder, Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics, J. Org. Chem, vol.76, pp.2386-2407, 2011.

A. Nowak-krol and F. Würthner, Progress in the synthesis of perylene bisimide dyes, Org. Chem. Front, vol.6, pp.1272-1318, 2019.

K. Chen and C. Chang, Highly soluble monoamino-substituted perylene tetracarboxylic dianhydrides: Synthesis, optical and electrochemical properties, Int. J. Mol. Sci, vol.15, pp.22642-22660, 2014.

H. Tsai, C. Chang, and K. Chen, 1,6-and 1,7-regioisomers of dinitro-and diamino-substituted perylene bisimides: Synthesis, photophysical and electrochemical properties, Tetrahedron Lett, vol.55, pp.884-888, 2014.

R. Wang, G. Li, A. Zhang, W. Wang, G. Cui et al., Efficient energy-level modification of novel pyran-annulated perylene diimides for photocatalytic water splitting, Chem. Commun, vol.53, pp.6918-6921, 2017.

L. Rocard, D. Hatych, T. Chartier, T. Cauchy, and P. Hudhomme, Original Suzuki-Miyaura Coupling Using Nitro Derivatives for the Synthesis of Perylenediimide-Based Multimers, Eur. J. Org. Chem, pp.7635-7643, 2019.

R. K. Gupta, D. S. Shankar-rao, S. K. Prasad, and A. S. Achalkumar, Columnar Self-Assembly of Electron-Deficient Dendronized Bay-Annulated Perylene Bisimides, Chem. Eur. J, vol.24, pp.3566-3575, 2018.

A. Goujon, L. Rocard, T. Cauchy, and P. Hudhomme, An Efficient Imine Photocyclization as an Alternative to the Pictet-Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes, 2020.

F. Würthner, Bay-substituted perylene bisimides: Twisted fluorophores for supramolecular chemistry, Pure Appl. Chem, vol.78, pp.2341-2349, 2006.

P. Rajasingh, R. Cohen, E. Shirman, L. J. Shimon, and B. Rybtchinski, Selective Bromination of Perylene Diimides under Mild Conditions, J. Org. Chem, vol.72, pp.5973-5979, 2007.

H. Langhals and S. Kirner, Novel fluorescent dyes by the extension of the core of perylenetetracarboxylic bisimides, Eur. J. Org. Chem, pp.365-380, 2000.

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

K. Chen and T. J. Chow, 1,7-Dinitroperylene bisimides: Facile synthesis and characterization as n-type organic semiconductors, Tetrahedron Lett, vol.51, pp.5959-5963, 2010.

K. Chen, T. Fang, and M. Chang, Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides, Dyes Pigm, vol.92, pp.517-523, 2012.

Z. J. Chen, L. M. Wang, G. Zou, L. Zhang, G. J. Zhang et al., Colorimetric and ratiometric fluorescent chemosensor for fluoride ion based on perylene diimide derivatives, Dyes Pigm, vol.94, pp.410-415, 2012.

Y. Wang, L. Zhang, G. Zhang, Y. Wu, S. Wu et al., A new colorimetric and fluorescent bifunctional probe for Cu2+ and F-ions based on perylene bisimide derivatives, Tetrahedron Lett, vol.55, pp.3218-3222, 2014.

H. Tsai and K. Chen, Synthesis and optical properties of novel asymmetric perylene bisimides, J. Lumin, vol.149, pp.103-111, 2014.

S. Rosenne, E. Grinvald, E. Shirman, L. Neeman, S. Dutta et al., Self-Assembled Organic Nanocrystals with Strong Nonlinear Optical Response, Nano Lett, vol.15, pp.7232-7237, 2015.

D. Meng, D. Sun, C. Zhong, T. Liu, B. Fan et al., High-Performance Solution-Processed Non-Fullerene Organic Solar Cells Based on Selenophene-Containing Perylene Bisimide Acceptor, J. Am. Chem. Soc, vol.138, pp.375-380, 2016.

P. Singh, K. Kumar, G. Bhargava, and S. Kumar, Self-assembled nanorods of bay functionalized perylenediimide: Cu2+ based 'turn-on' response for INH, complementary NOR/OR and TRANSFER logic functions and fluorosolvatochromism, J. Mater. Chem. C, vol.4, pp.2488-2497, 2016.

K. Kumar, G. Bhargava, S. Kumar, and P. Singh, Dissymmetric Bay-Functionalized Perylenediimides, Synlett, vol.29, pp.1693-1699, 2018.

P. Singh, L. S. Mittal, V. Vanita, K. Kumar, A. Walia et al., Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: Reaction-based near-IR intracellular fluorescent probe for selective detection of palladium, J. Mater. Chem. B, vol.4, pp.3750-3759, 2016.

A. D. Hendsbee, J. Sun, W. K. Law, H. Yan, I. G. Hill et al., Synthesis, Self-Assembly, and Solar Cell Performance of N-Annulated Perylene Diimide Non-Fullerene Acceptors, Chem. Mater, vol.28, pp.7098-7109, 2016.

R. El-berjawi and P. Hudhomme, Synthesis of a perylenediimide-fullerene C60 dyad: A simple use of a nitro leaving group for a Suzuki-Miyaura coupling reaction, Dyes Pigm, vol.159, pp.551-556, 2018.

M. Hruzd, L. Rocard, M. Allain, P. Hudhomme, and . Suzuki-miyaura, Coupling on Dinitro-bay Substituted Perylenediimide, 2020.

H. Tsai, C. Chang, and K. Chen, 1,6-and 1,7-regioisomers of asymmetric and symmetric perylene bisimides: Synthesis, characterization and optical properties, Molecules, vol.19, pp.327-341, 2014.

R. K. Dubey, A. Efimov, and H. Lemmetyinen, 1,7-And 1,6-Regioisomers of Diphenoxy and Dipyrrolidinyl Substituted Perylene Diimides: Synthesis, Separation, Characterization, and Comparison of Electrochemical and Optical Properties, Chem. Mater, vol.23, pp.778-788, 2011.

X. Kong, J. Gao, T. Ma, M. Wang, A. Zhang et al., Facile synthesis and replacement reactions of mono-substituted perylene bisimide dyes, Dyes Pigm, vol.95, pp.450-454, 2012.

D. Sun, D. Meng, Y. Cai, B. Fan, Y. Li et al., Non-Fullerene-Acceptor-Based Bulk-Heterojunction Organic Solar Cells with Efficiency over 7%, J. Am. Chem. Soc, vol.137, pp.11156-11162, 2015.

M. Nazari, E. Cieplechowicz, T. A. Welsh, and G. C. Welch, A direct comparison of monomeric vs. dimeric and non-annulated vs. N-annulated perylene diimide electron acceptors for organic photovoltaics, New J. Chem, vol.43, pp.5187-5195, 2019.

Z. Ma, H. Fu, D. Meng, W. Jiang, Y. Sun et al., Isomeric N-Annulated Perylene Diimide Dimers for Organic Solar Cells, Chem. Asian J, vol.13, pp.918-923, 2018.

J. R. Cann, C. Cabanetos, and G. C. Welch, Synthesis of Molecular Dyads and Triads Based Upon N-Annulated Perylene Diimide Monomers and Dimers, Eur. J. Org. Chem, pp.6933-6943, 2018.
URL : https://hal.archives-ouvertes.fr/hal-02327306

L. Chen, P. Xia, T. Du, Y. Deng, and Y. Xiao, Catalyst-Free One-Pot Synthesis of Unsymmetrical Fiveand Six-Membered Sulfur-Annulated Heterocyclic Perylene Diimides for Electron-Transporting Property, Org. Lett, vol.21, pp.5529-5532, 2019.

Y. Ma, Z. Shi, A. Zhang, J. Li, X. Wei et al., Self-assembly, optical and electrical properties of five membered O-or S-heterocyclic annulated perylene diimides, Dyes Pigm, vol.135, pp.41-48, 2016.

R. Wang, G. Li, Y. Zhou, P. Hao, Q. Shang et al., Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides, Asian J. Org. Chem, vol.7, pp.702-706, 2018.

X. Li, H. Wang, H. Nakayama, Z. Wei, J. A. Schneider et al., Multi-Sulfur-Annulated Fused Perylene Diimides for Organic Solar Cells with Low Open-Circuit Voltage Loss, ACS Appl. Energy Mater, vol.2, pp.3805-3814, 2019.

Y. Yang, Palladium-Catalyzed Cross-Coupling of Nitroarenes, Angew. Chem. Int. Ed, vol.56, pp.15802-15804, 2017.

M. R. Yadav, M. Nagaoka, M. Kashihara, R. Zhong, T. Miyazaki et al., The Suzuki-Miyaura Coupling of Nitroarenes, J. Am. Chem. Soc, vol.139, pp.9423-9426, 2017.

L. Rocard and P. Hudhomme, Recent developments in the Suzuki-Miyaura reaction using nitroarenes as electrophilic coupling reagents. Catalysts, vol.9, p.213, 2019.

S. Aivali, L. Tsimpouki, C. Anastasopoulos, and J. K. Kallitsis, Synthesis and optoelectronic characterization of perylene diimide-quinoline based small molecules, Molecules, vol.24, p.4406, 2019.

H. Tsai and K. Chen, 1,7-Diaminoperylene bisimides: Synthesis, optical and electrochemical properties, Dyes Pigm, vol.96, pp.319-327, 2013.

L. Hao, W. Jiang, and Z. Wang, Integration of nitrogen into coronene bisimides, Tetrahedron, vol.68, pp.9234-9239, 2012.

G. Li, Y. Zhao, J. Li, J. Cao, J. Zhu et al., Synthesis, Characterization, Physical Properties, and OLED Application of Single BN-Fused Perylene Diimide, J. Org. Chem, vol.80, pp.196-203, 2015.

L. Zhang, Y. Wang, J. Yu, G. Zhang, X. Cai et al., A colorimetric and fluorescent sensor based on PBIs for palladium detection, Tetrahedron Lett, vol.54, pp.4019-4022, 2013.

M. Schulze, M. Philipp, W. Waigel, D. Schmidt, and F. Wuerthner, Library of Azabenz-Annulated Core-Extended Perylene Derivatives with Diverse Substitution Patterns and Tunable Electronic and Optical Properties, J. Org. Chem, vol.81, pp.8394-8405, 2016.

J. Shi, J. Fan, Z. Qu, S. Wang, and Y. Wang, Solution concentration-dependent tunable emission in cyclometalated iridium complex bearing perylene diimide (PDI) ligand: From visible to near-infrared emission, Dyes Pigm, vol.154, pp.263-268, 2018.

M. Schulze, A. Steffen, and F. Wuerthner, Near-IR Phosphorescent Ruthenium(II) and Iridium(III) Perylene Bisimide Metal Complexes, Angew. Chem. Int. Ed, vol.54, pp.1570-1573, 2015.

, This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license, © 2020 by the authors. Licensee MDPI