In this paper, some derivatives of perylene bisimides are successfully synthesized and characterized using FTIR, HNMR and XRD techniques. In addition, their UV–Vis–NIR reflectance spectra are investigated. Synthesized pigments were planned to have high structural similarities as all of them were N,N′-diphenyl-3,4,9,10-perylenedicarboximide derivatives. The substituents are selected from two categories including activating groups and deactivating ones. The correlation between substituent electronic properties and NIR features of the synthesized pigments is investigated, while the data of three previously synthesized derivatives are included. The results have revealed interesting approximate correlation between NIR properties and electronic features of the substituents. Electronically activating groups reduce the reflectance values (on white substrate) of the pigments in comparison with nonsubstituted molecule, while deactivating ones increase the reflectance amount. This result can be a starting point for detailed studying of structure–NIR properties correlation in perylene pigments. Crystallinity (%) of the pigments is estimated using XRD patterns, and the probable correlation of this parameter with NIR properties of the pigments is investigated, and no meaningful correlation is detected. All the pigments are NIR-transparent and subsequently are capable to be used as cool pigments.
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Ascione, F, “Energy Conservation and Renewable Technologies for Buildings to Face the Impact of the Climate Change and Minimize the Use of Cooling.” Sol. Energy, 154 34–100 (2017)
Rosenfeld, AH, Akbari, H, Bretz, S, Fishman, BL, Kurn, DM, Sailor, D, Taha, H, “Mitigation of Urban Heat Islands: Materials, Utility Programs, Updates.” Energy Build., 22 255–265 (1995)
Santamouris, M, Ding, L, Fiorito, F, Oldfield, P, Osmond, P, Paolini, R, Prasad, D, Synnefa, A, “Passive and Active Cooling for the Outdoor Built Environment—Analysis and Assessment of the Cooling Potential of Mitigation Technologies Using Performance Data from 220 Large Scale Projects.” Sol. Energy, 154 14–33 (2017)
Zinzi, M, Carnielo, E, Agnoli, S, “Characterization and Assessment of Cool Coloured Solar Protection Devices for Mediterranean Residential Buildings Application.” Energy Build., 50 111–119 (2012)
Jiang, L, Xue, X, Qu, J, Qin, J, Song, J, Shi, Y, “The Methods for Creating Energy Efficient Cool Gray Building Coatings—Part II: Preparation from Pigments of Complementary Colors and Titanium Dioxide Rutile.” Sol. Energy Mater. Sol. Cells, 130 410–419 (2014)
Zhang, W, Song, Z, Shi, Y, Song, J, Qu, J, Qin, J, “The Effects of Manufacturing Processes and Artificial Accelerated Weathering on the Solar Reflectance and Cooling Effect of Cool Roof Coatings.” Sol. Energy Mater. Sol. Cells, 118 61–71 (2013)
Song, J, Qin, J, Qu, J, Song, Z, Zhang, W, Xue, X, Shi, Y, Zhang, T, Ji, W, Zhang, R, Zhang, H, Zhang, Z, Wu, X, “The Effects of Particle Size Distribution on the Optical Properties of Titanium Dioxide Rutile Pigments and their Applications in Cool Non-white Coatings.” Sol. Energy Mater. Sol. Cells, 130 42–50 (2014)
Pomerantz, M, “Are Cooler Surfaces a Cost-Effect Mitigation of Urban Heat Islands?” Urban Clim., (2017). https://doi.org/10.1016/j.uclim.2017.04.009
Synnefa, A, Santamouris, M, Apostolakis, K, “On the Development, Optical Properties and Thermal Performance of Cool Colored Coatings for the Urban Environment.” Sol. Energy, 81 488–497 (2007)
Levinson, R, Berdahl, P, Akbari, H, “Solar Spectral Optical Properties of Pigments—Part I: Model for Deriving Scattering and Absorption Coefficients from Transmittance and Reflectance Measurements.” Sol. Energy Mater. Sol. Cells, 89 319–349 (2005)
Mastrapostoli, E, Santamouris, M, Kolokotsa, D, Vassilis, P, Venieri, D, Gompakis, K, “On the Ageing of Cool Roofs: Measure of the Optical Degradation, Chemical and Biological Analysis and Assessment of the Energy Impact.” Energy Build., 114 191–199 (2015)
Herbst, W, Hunger, K, Industrial Organic Pigments. VCH-Elsevier, Amsterdam (1997)
Oh, SH, Kim, BG, Yun, SJ, Maheswara, M, Kim, K, Do, JY, “The Synthesis of Symmetric and Asymmetric Perylene Derivatives and their Optical Properties.” Dyes Pigm., 85 37–42 (2010)
Kozma, E, Catellani, M, “Perylene Diimides Based Materials for Organic Solar Cells.” Dyes Pigm., 98 (1) 160–179 (2013)
Türkmen, G, Erten-Ela, S, Icli, S, “Highly Soluble Perylene Dyes: Synthesis, Photophysical and Electrochemical Characterizations.” Dyes Pigm., 83 (3) 297–303 (2009)
Kaur, B, Quazi, N, Ivanov, I, Bhattacharya, SN, “Near-Infrared Reflective Properties of Perylene Derivatives.” Dyes Pigm., 92 (3) 1108–1113 (2012)
Kaur, B, Bhattacharya, SN, Henry, DJ, “Interpreting the Near-Infrared Reflectance of a Series of Perylene Pigments.” Dyes Pigm., 99 502–511 (2013)
Mazhar, M, Abdouss, M, Gharanjig, K, Teimuri-mofrad, R, “Synthesis, Characterization and Near Infra-Red Properties of Perylene Bisimide Derivatives.” Prog. Org. Coat., 101 297–304 (2016)
Mazhar, M, Abdouss, M, Gharanjig, K, Teimuri-mofrad, R, Zargaran, M, “Effects of Isomerism on Near Infrared Properties of Perylene Bisimide Derivatives.” J. Coat. Technol. Res., 14 207–214 (2017)
Brady, RF, Wake, LV, “Principles and Formulations for Organic Coatings with Tailored Infrared Properties.” Prog. Org. Coat., 20 1–25 (1992)
ASTM G173-03(2012), Standard Tables for Reference Solar Spectral Irradiances: Direct Normal and Hemispherical on 37° Tilted Surface, ASTM International, West Conshohocken, PA, 2012, www.astm.org
Vishnu, VS, Reddy, ML, “Near Infrared Reflecting Inorganic Pigments Based on Molybdenum and Praseodymium Doped Yttrium Cerate: Synthesis, Characterization and Optical Properties.” Sol. Energy Mater. Sol. Cells, 95 2685–2692 (2011)
Thongkanluang, T, Kittiauchawal, T, Limsuwan, P, “Preparation and Characterization of Cr2O3–TiO2–Al2O3–V2O5 Green Pigment.” Ceram. Int., 37 543–548 (2011)
Gartland, L, Heat Islands, Understanding and Mitigating Heat in Urban Areas. Earthscan, London (2008)
Black, DB, Lovering, EG, “Estimation of the Degree of Crystallinity in Digoxin by X-ray and Infrared Methods.” J. Pharm. Pharmacol., 29 684–687 (1977)
Shah, B, Kakumanu, VK, Bansal, AK, “Analytical Techniques for Quantification of Amorphous/Crystalline Phases in Pharmaceutical Solids.” J. Pharmacol. Sci., 95 (8) 1641–1665 (2006)
The financial support of this work by the Research Council of Amirkabir University of Technology (Tehran Polytechnic) is gratefully acknowledged.
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Mahmoudi Meymand, F., Mazhar, M. & Abdouss, M. Investigation of substituent effect on cool activity of perylene bisimide pigments. J Coat Technol Res 16, 439–447 (2019). https://doi.org/10.1007/s11998-018-0122-z
- Perylene derivatives
- NIR reflective
- NIR transparent
- Cool pigments
- NIR–constitution correlation