A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Yıl 2017, Cilt: 13 Sayı: 2, 379 - 386, 30.06.2017

Özgür Birel

https://doi.org/10.18466/cbayarfbe.319879

Cited By: 3

Öz

The aim of this
article is to inform about perylene-3,4,9,10-tetracarboxylic acid dimide (PDI)
derivatives. Also, it is to give short and simple information about optical
properties and using fields. Perylene-3,4,9,10-tetracarboxylic acid dimide
derivatives known as perylene diimides are material
of highly conjugated molecule. PDIs exhibit strong absorptions within
the range of 400-450 nm (B band) and 500-700 nm (Q band). Perylene diimide dyes show generally characteristic
absorption peaks at 458, 490, 526 nm. These absorption peaks are matched by the
corresponding emission peaks at 540, 576, 624 nm, respectively. It has donor
core and acceptor carbonyl groups. Perylene dimide has good electron
mobility, high fluorescence quantum yields, strong absorption in the visible
region, photostability, thermal
stability,  good semi-conductivity. These properties
benefit them application of electronic material. Applications of PDIs are in
the field of photo-electronic material, dye lasers, organic light-emitting diodes,
and chemosensing materials.

Anahtar Kelimeler

Dye, Organic based-solar cells (DSSC), perylene diimide, perylene monoimide, sensor

Kaynakça

• [1] Aleshinloye, A.O.; Bodapati, J. B.; Icil, H. Synthesis, Characterization, Optical and Electrochemical Proper-ties of a New Chiral Multichromophoric System Based on Perylene and Naphthalene Diimides. Journal of Photochemistry and PhotobiologybA: Chemistry. 2015; 300, 27-37.
• [2] Huang, C.; Barlow, S.; Marder, S.R. Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics. The Journal of Organic Chemistry. 2011; 76, 2386-2407.
• [3] Zhao,H.; Zhang, Y.; Xu, H.; He, Z.; Zhang, Z.; Zhang, H. Synthesis and Properties of Perylene Diimide Dyes Bearing Unsymmetrical and Symmetrical Phenoxy Substituents at Bay Positions. Tetrahedron. 2015; 71, 7752-7757.
• [4] Saeed, A.; Shabir, G.; Mahar, J.; Irfan, M. Spectro-scopic and Electrochemical Behavior of Newly Synthe-sized High Fluorescent Symmetric 4′-nitrophenyl-3,4,9,10-perylenebisdiimide-azo Hybrid Dyes. Spectro-chimica Acta Part A: Molecular and Biomolecular Spec-troscopy. 2015; 151, 72-79.
• [5] Rachford, A.A.; Goeb, S.; Castellano, F.N. Accesing the Excited State in Perylenediimides. American Chem-ical Society. 2008; 130, 2766-2767.
• [6] Georgiev, N.I.; Sakr, A.R.; Bojinov.V.B. Design and Synthesis of Novel Fluorescence Sensing Perylene Diimides Based on Photoinduced Electron Transfer. Dyes and Pigments. 2011; 91, 332-339.
• [7] Handa, N.V.; Mendoza, K.D.; Shietcliff, L.D. Synthe-ses and Properties of 1,6 and 1,7 Perylenediimides and Tetracarboxylic Dianhydrides. Org.Lett. 2011; 13(17), 332-339.
• [8] Boobalan, G.; Imran, P.M.; Nagarajan, S. Synthesis of Highly Fluorescent and Water Soluble Perylene Bisi-mide. Chinese Chemical Letters. 2012; 23, 149-153.
• [9] Liu,Y.; Wang, Y.; Ai, L.; Liu, Z.; Ouyang, X.; Ge, Z. Perylenebisimide Regioisomers: Effect of Substituent Position on Their Spectroscopic, Electrochemical, and Photovoltaic Properties. Dyes and Pigments. 2015; 121, 363-371.
• [10] Zhang, R.; Wang, Z.; Wu, Y.; Fu, H.; Yao, J. A Novel Redox-Fluorescence Switch Based on a Triad Contain-ing Ferrocene and Perylene Dimide Units. Org.Lett. 2008; 121(10), 3065-3068.
• [11] Handa, N.V.; Shirtcliff, L.D.; Berlin, K.D. Synthesis, Photophysical, and Electrochemical Properties of Ham-ilton Receptor Functionalized Perylene Diimides. Tet-rahedron Letters. 2015; 56, 445-451.
• [12] Lv, Z.; Liu, J.; Bai, W.; Yang, S.; Chen, A. A Simple and Sensitive Label-Free Fluorescent Approach for Pro-tein Detection Based on a Perylene Probe and Aptamer. Biosensors and Bioelectronics. 2015; 64, 530-534.
• [13] Dias, M.; Hudhomme, P.; Levillain, E.; Perrin, L.; Sahin, Y.; Sauvage, F.; Wartelle, C. Electrochemistry Coupled to Fluorescence Spectroscopy: a New Versatile Approach. Electrochemistry Communications. 2004; 6, 325-330.
• [14] Lee, S.K.; Zu, Y.; Herrmann, A.; Geerts, Y.; Müllen, K.; and Bard, A.J. Electrochemistry, Spectroscopy and Electrogenerated Chemiluminescence of Perylene, Ter-rylene, and Quaterrylene diimides in Aprotic Solution. J.Am.Chem.Soc. 1999; 121, 3513-3520.
• [15] Yu, Y.; Li, Y.; Qin, Z.; Jiang, R.; Liu, H.; Li, Y. De-signed Synthesis and Supramolecular Architectures of furan-substituted Perylene Dimide. Journal of Colloid and Interface Science. 2013; 399, 13-18.
• [16] Tahir, M.; Sayyad, M.H.; Wahab, F.; Aziz, F.; Shahid, M.; Munawar, M.A. Perylene Diimide: Synthesis, Fabri-cation and Temperature Dependent Electrical Charac-terization of Heterojunction with p-silicon. Physica B: Condensed Matter. 2013; 426, 6-12.
• [17] Mikroyannidis, J.A.; Stylianakis, M.M.; Sharma, G.D.; Balraju, P.; Roy, M.S. A novel Alternating Phe-nylenevinylene Copolymer with Perylene Bisimide Units: Synthesis, Photophysical, Electrochemical, and Photovoltaic Properties. J.Phys.Chem.C. 2009; 113, 7904-7912.
• [18] Kaya, İ.; Koyuncu, S.; Çulhaoğlu, S. Synthesis and Characterization of Novel Polyazomethines Containing Perylene Units. Polymer. 2008; 49, 703-714.
• [19] Chen, Y.; Kong, Y.; Wang, Y.; Ma, P.; Bao, M.; Li, X. Supramolecular Self-assembly Study of a Flexible Perylenetetracarboxylic Dimide Dimer in Langmuir and Langmuir-blodgett Films. Journal of Colloid and Interface Science. 2009; 330, 421-427.
• [20] Dinçalp, H.; Çimen, O.; Ameri, T.; Brabec, C.J.; İçli, S. Synthesis, Characterization and Optoelectronic Properties of a New Perylene diimide–benzimidazole Type Solar Light Harvesting Dye. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014; 128, 197-206.
• [21] Birel, O.H.; Zafer, C.; Dincalp, H.; Aydın, B.; Can, M. Highly Soluble Polyoxyethylene-perylene Diimide: Optical, Electrochemical and Photovoltaic Studies. J.Chem.Soc.Pak. 2011; 33(4), 562-569.
• [22] Zhang, X.; Pang, S.; Zhang, Z.; Ding, X.; Zhang, S.; He, S.; Zhan, C. Facile Synthesis of 1-bromo-7-alkoxyl Perylene Diimide Dyes: Toward Unsymmetrical Func-tionalizations at the 1,7-positions. Tetrahedron Letters. 2012; 53, 1094-1097.
• [23] Sivamurugan, V.; Kazlauskas, K.; Jursenas, S.; Gru-odis, A.; Simokaitiene, J.; Grazulevicius, J.V.; Valiya-veettil, S. Synthesis and Photophysical Properties of Glass-forming Bay-substituted Perylenediimide Deriva-tives. J.Phys.Chem. 2010; 114, 1782-1789.
• [24] Balaji, G.; Kale, T.S.; Keerthi, A.; Pelle, A.M.D.; Tha-yumanavan, S.; and Valiyaveettil, S. Low Band Gap Thiophene-perylene Diimide Systems with Tunable Charge Transport Properties. Organic Letters. 2011; 13(1), 18-21.
• [25] Haklı, Ö., Synthesis of Perylene Dimide Derivatives and Studies on Photophysical Properties of Perylene Diimides and Some Vitamine-K3 Derivatives: Stability Tests Under Concentrated Sun Light (Ph.D. thesis), Ege University.Chemistry Department, Izmir. 2006.
• [26] Yang, L.; Shi, M.; Wang, M.; Chen, H. Synthesis, Electrochemical, and Spectroscopic Properties of Solu-ble Perylene Monoimide Diesters. Tetrahedron. 2008; 64, 5404-5409.
• [27] Bryaskova, R.; Georgiev, N.I.; Dimov, S.M.; Tzoneva, R.; Detrembleur, C.; Asiri, A.M.; Alamry, K.A.; Bojinov, V.B. Novel Nanosized Water Soluble Fluorescent Mi-celles with Embedded Perylene Diimide Fluorophores for Potential Biomedical Applications: Cell Permeabil-ity, Localization and Cytotoxicity. Materials Science and Engineering: C. 2015; 51, 7-15.
• [28] Wang, J.; Zhong, S.; Duan, W.; Gao, B. Fluorinated Perylene Diimides: Synthesis, Electrochemical-Photophysical Properties, and Cellular Imaging. Tetra-hedron Letters. 2015; 56, 824-827.
• [29] Zhou, X.; Liu, D.; Wang, T.; Hu, X.; Guo, J.; We-erasinghe, K.C.; Wang, L.; Li, W. Synthesis and Photo-physical Studies of Triazine-linked Porphyrin-Perylene Bisimide Dyad with Long-lived Perylene Triplet State. Journal of Photochemistry and Photobiology A: Chem-istry. 2014; 274 ,57-63.
• [30] Cheng, H.R.; Qian, Y. Two Novel Rhodamine-Perylenediimide Fluorescent Probes: Synthesis, Photo-physical Properties, and Cell Imaging. Chinese Chemi-cal Letters. 2016; http://dx.doi.org/10.1016/j.cclet.2016.01.039.
• [31] Zhao, X.H.; Gong, L.; Wu, Y.; Zhang, X.B.; Xie, J. Cationic-perylene-G-quadruplex Complex Based Fluo-rescent Biosensor for Label-free Detection of Pb2+. Talan-ta. 2016; 149, 98-102.
• [32] Cheng, H.; Qian, Y. Intramolecular Fluorescence Resonance Energy Transfer in a Novel PDI-BODIPY Dendritic Structure: Synthesis, Hg2+ Sensor and Living Cell Imaging. Sensors and Actuators B. 2015; 219,57-64.
• [33] Wang, Y.; Zhang, L.; Zhang, G.; Wu, Y.; Wu, S.; Yu, J.; Wang, L. A New Colorimetric and Fluorescent Bi-functional Probe for Cu2+ and F- Ions Based on Perylene Bisimide Derivatives. Tetrahedron Letters. 2014; 55, 3218-3222.
• [34] Birel Ö., An Overwiew on the Some Phenothizanie Derivative Molecules used in Organic Dye-sensitized Solar Cells. Electronic Journal of Vocational Colleges. 2015.
• [35] Kozma, E.; Kotowski, D.; Catellani, M.; Luzzati, S.; Famulari, A.; Bertini, F.S ynthesis and Characterization of New Electron Acceptor Perylene Dimide Molecules for Photovoltaic Applications. Dyes and Pigments, 2013; 99, 329-338.
• [36] Jeonga, S.; Hana, Y.S.; Kwonb, Y.; Choic, M.S.; Chod, G.; Kime, K.S.; Kimd, Y. Effects of n-type Perylene De-rivative as an Additive on the Power Conversion Effiencies of Polymer Solar Cells. Synthetic Metals, 2010; 160, 2109-2115
• [37] Jin, Y.; Hua, J.; Wu, W.; Ma, X.; Meng, F. Synthesis, Characterization and Photovoltaic Properties of Two Novel Near-infrared Absorbing Perylene Dyes Contain-ing benzo[e]indole for Dye-sensitized Solar Cells. Syn-thetic Metals, 2008; 158, 64-71.
• [38] Tahir,M.; Sayyad, M.H.; Wahab, F.; Aziz, F.; Shahid, M.; Munawar, M.A.; Perylene Dimide: Synthesis, Fabri-cation and Temperature Dependent Electrical Charac-terization of Heterojunction with p-silicon. Physica B. 2013; 426, 6–12.