21 September 2017 - پنج شنبه 30 شهريور 1396
جستجوی مقالات
کلید واژگان
جستجوی پیشرفته
شناسنامه ی نشریه
صاحب امتیاز:
موسسه پژوهشی علوم و فناوری رنگ و پوشش
مدیر مسئول:
پروفسور زهرا رنجبر
سردبیر:
دکتر شهره روحانی
مدیر اجرایی:
دکتر مریم عطائی فرد
شاپا چاپی:
2251-7278
شاپا الکترونیکی:
2383-2223
دسترسی سریع
آخرین شماره ها
نظر سنجی
نظر شما در مورد سایت نشریه دنیای رنگ چیست؟
مطلوب
نسبتا مطلوب
نیاز به بهسازی دارد
ضعیف

ارتباط رنگ و ساختار مواد رنگزای آلی: مروری بر بیش از یک قرن پژوهش

نشریه: سال چهارم- شماره سوم- پاييز 1393 - مقاله 9   صفحات :  85 تا 103



کد مقاله:
JSCW-18-05-2014-10162

مولفین:
صادق مهویدی: موسسه پژوهشي علوم و فناوري رنگ و پوشش - گروه پژوهشي مواد رنگزای آلی
علی آشتیانی عبدی: موسسه پژوهشي علوم و فناوري رنگ و پوشش - گروه پژوهشي مواد رنگزای آلی
فرحناز نورمحمدیان: موسسه پژوهشي علوم و فناوري رنگ و پوشش - گروه پژوهشي مواد رنگزای آلی


چکیده مقاله:



ارتباط بین رنگ و ساختار ملکولی مواد رنگزای آلی برای مدت طولانی، موضوعی بسیار مورد علاقه هم برای شیمیدانان مشغول در زمینه ترکیبات آلی و هم شیمیدانان تئوریسین¬ بوده است. به دلیل اهمیت این موضوع، از زمان ارائه اولین تئوری در مورد گروه-های کروموفور¬ و آگزوکروم¬ توسط آقای ویت تقریباً بیش از یک قرنِ پیش تعداد زیادی از مقالات در مورد این مطلب در نشریات علمی چاپ گردیده است. پیدایش نظریه کوانتوم تا حد زیادی پیشرفت در این زمینه را شتاب داده است و همچنین ثابت گردیده که توسعه نهایی روش های کمی جهت پیش بینی¬های اسپکتروسکوپی طیفی از ارزش عملی قابل توجهی در جستجو برای مواد رنگزای جدید برخوردار می¬باشد. بدیهی است امروزه، شیمیدان رنگ در جایگاه پیش بینی طیف جذبی مرئی هر ملکول کانجوگه، هر چند پیچیده و حتی بدون دقت بالا می¬باشند. با وجود اهمیت آشکار مطالعات در زمینه رنگ و ساختار، تا چند سال پیش مقالات مروری بسیار کمی در این مورد یافت می¬شد. هدف این مقاله مروری، بررسی تاریخچه و پیشرفت¬های مبحث ارتباط رنگ و ساختار، آشنایی با روش¬های مختلف در این زمینه با تمرکز بر مواد رنگزای آلی در مباحث تئوری و عملی می¬باشد.


Article's English abstract:

Relationships between the colour and constitution of organic dyes have long been a subject of great interest to both theoretical and organic chemists and as a consequence a vast number of publications on this subject have appeared in the scientific literature since Witt first proposed his theory of chromophores and auxochromic groups more than a century ago. The advent of quantum theory greatly accelerated progress in this field and the eventual development of quantitative methods for spectroscopic predictions has proved to be of considerable practical value in the search for new dyes. Certainly today the colour chemist is in a position to predict the visible absorption spectrum of any conjugated molecule, however complex, if not with high precision, at least with some confidence as to the general appearance of the spectrum relative to some model chromogen. In spite of the obvious importance of colour and constitution studies, general review papers on this topic have been relatively scarce up until a few years ago. This paper will review the history and development of color and constitution issue and introduce various theoretical and practical methods in this area with a focus on organic dyes in discussions.


کلید واژگان:
ارتباط بين رنگ و ساختار مواد، مواد رنگزای آلی، شیمی محاسباتی، روش‌های نیمه تجربی، روش‌های اوربیتال مولکولی.

English Keywords:
Color and constitution, Organic dyes, Computational chemistry, Semi-empirical methods, Molecular orbital methods.

منابع:

English References:
1.J. Griffiths, "Colour and Constitution of organic molecules", London; Academic Press, 1976.#2.J. Griffiths, "Recent developments in the Colour and Constitution of Organic dyes", Rev. Prog. Coloration, 11, 37-57, 1981.#3.J. Griffiths, "Practical aspects of Colour prediction of Organic dye molecules", Dyes and pigments, 3, 211-233, 1982.#4.M. J. S. Dewar, "Colour and Constitution. Part I. Basic dyes", J. Chem. Soc., 2329-2334, 1950.# 5.M. J. S. Dewar, "Colour and Constitution. Part II. Aromatic hydrocarbons", J. Chem. Soc., 3532-3544, 1952.#6.M. Klessinger, "Konstitution und lichtabsorption organischer Farbstoffe", Chemie in unserer Zeit, 12. 1-11, 1978.#7.S. D?hne, "Color and Constitution: One hundred years of Research", Science, 199, 17, 1163-1167, 1978.#8.O. N. Witt, "To the knowledge of the structure and the formation of Coloring carbon compounds", Ber. Dtsch. Chem. Ges. 9, 522-527, 1876.#9.W. K?nig, "On the concept of "polymethine" and a derivable general dye formula as a basis for a new classification of color chemistry", J. Prakt. Chem. 112, 1-36, 1926.#10.G. Scheibe, W. Seiffert, H. Wengenmayr, C. Jutz, "Proton resonance studies of cyanine dyes", Ber. Bunsenges. Phys. Chem. 67, 6, 560-570, 1963.#11.Z. Yoshida, F. Takabayashi, "Electronic spectra of mono-substituted anthraquinones and solvent effects", Tetrahedron, 24, 933-943, 1968.#12.L. P. Hammett, "Physical Organic Chemistry", New York, McGraw-Hill, 1970.# 13.I. Bridgeman, A. T. Peters, "Synthesis and electronic spectra of some 4-aminoazobenzenes", J. Soc. Dyers Colourists, 86, 519-524, 1970.#14.F. Gerson, E. Heilbronner, "Electronic structure and physico-chemical properties of azo compounds Part V: On the influence of substituents on the absorption spectrum of phenyl-azo-azulene, a contribution to the knowledge of the PLATTNER'schen shift rule", Helv. chim. Acta, 42, 6, 1877-1908, 1959.#15.T. Hayashi, M. Matsuo, "Studies on the Effects of the Substituents for 1-Arylaminoanthraquinones", 35, 9,1500-1506, 1962.#16.C. C. Barker, M. H. Bride, G. Hallas, A. Stamp, "Steric effects in di- and tri-arylmethanes. Part III. Electronic absorption spectra of derivatives of Malachite Green containing substituents in the phenyl ring", J. Chem. Soc., 1285-1290, 1961.#17.J. Griffiths, "Prediction of colour change in dye Equilibria I-Azo and hydrazone tautomers and anions of 4-phenylazo-1-naphthols", JSDC, 88, 3,106-109, 1972.# 18.L. A. Jones, C. Kinney Hancock, "Spectrophotometric studies of some 2, 4-dinitrophenylhydrazones. III.1 Taft and Hammett Relationships", J. Org. Chem., 25, 2, 226-231, 1960.#19.H. Labhart, "For the quantitative description of the influence of substituents on the absorption spectrum of molecules of flat. application to anthraquinone", Helv. chim. Acta. 40, 5, 1410-1420, 1957.#20.R. Grinter and E. Heilbronner, "Energy and charge distribution of electronically excited states of polysubstituted benzenes: A quantum-chemical interpretation of the witt dilthey-wizinger'schen color rules", Helv. chim. Acta., 45, 7, 2496-2516, 1962.# 21.J. Griffiths, M. Lockwood, B. Roozpeikar, "Orientation effects in the benzene chromophore bearing one donor and two acceptor groups. Electronic absorption spectra of the dicyanoanilines", J. Chem. Soc., Perkin Trans. 2, 1608-1610, 1977.# 22.J. Griffiths, B. Roozpeikar, "Synthesis and electronic absorption spectra of dicyano-derivatives of 4-diethylaminoazobenzene", J. Chem. Soc., Perkin Trans. 1, 42-45, 1976.# 23.M. J. S. Dewar, R. C. Dougherty, "The PMO Theory of Organic Chemistry", New York, Plenum, 1975.#24.M. J. S. Dewar, "Colour and constitution. Part I. Basic dyes", J. Chem. Soc., 2329-2334, 1950.#25.M. J. S. Dewar, "Steric Effects in Conjugated Systems", Ed.Gray, London, Butterworth, 46., 1958.# 26.R. Pariser, R. G. Parr, "A Semi-empirical theory of the" Electronic Spectra and Electronic Structure of Complex Unsaturated Molecules. II", J. Chem. Phys. 21, 767, 1953.#27.J. A. Pople, "Electron interaction in unsaturated hydrocarbons", Trans. Faraday Soc., 49, 1375-1385, 1953.#28.A. D. Laurent, C. Adamo, D. Jacquemin, "Dye chemistry with time-dependent density functional theory", Phys. Chem. Chem. Phys. 2014.#29.J. Fabian, H. Hartmann, "Reactivity and Structure Concepts in Organic Chemistry, Light Absorption of Organic Colorants", Springer-Verlag, Berlin, V. 12, 1980.#30.F. J. Green, "The Sigma-Aldrich Handbook of Stains, Dyes and Indicators", Aldrich Chemical Company, Inc, Milwaukee, Wisconsin, 1990.#31.R. M. Christie, "Colour Chemistry", The Royal Society of Chemistry, Cambridge, UK, p. 228, 1991.#32.J. Shore, D. Patterson, G. Hallas, "Colorants and auxiliaries", Society of Dyers and Colourists, Hampshire, UK, 2nd edn, 2002.#33.K. Hunger, "Industrial Dyes", Wiley-VCH, Weinheim, 2003.#34.H. Zollinger, "Color Chemistry, Syntheses, Properties and Applications of Organic Dyes and Pigments", Wiley-VCH, Weinheim, 3rd edn, p. 647, 2003.# 35.L. Rustioni, F. D. Meo, M. Guillaume, O. Failla, P. Trouillas, "Tuning color variation in grape anthocyanins at the molecular scale", Food Chem., 141, 4349-4357, 2013.#36.E. A. Perpe`te, V. Wathelet, J. Preat, C. Lambert, D. Jacquemin, "Toward a theoretical quantitative estimation of the ?max of Anthraquinones-based dyes", J. Chem. Theory Comput., 2, 434-440, 2006.#37.B. Le Guennic, O. Maury, D. Jacquemin, "Aza-boron-dipyrromethene dyes: TD-DFT benchmarks, spectral analysis and design of original near-IR structures", Phys. Chem. Chem. Phys., 14, 157-164, 2012.#38.D. Jacquemin, J. Preat, E. A. Perpe`te, D. P. Vercauteren, J.-M. Andre´, I. Ciofini, C. Adamo, "Absorption spectra of azobenzenes simulated with time-dependent density functional theory", Int. J. Quantum Chem., 111, 4224-4240, 2011.#39.D. Jacquemin, E. A. Perpe`te, I. Ciofini, C. Adamo, "On the TD-DFT UV/vis spectra accuracy: the azoalkanes", Theor. Chem. Acc., 120, 405-410, 2008.#40.J. Preat, D. Jacquemin, V. Wathelet, J. M. Andre´, E. A. Perpe`te, "TD-DFT investigation of the UV spectra of pyranone derivatives", J. Phys. Chem. A, 110, 8144-8150, 2006.#41.B. Champagne, M. Guillaume, F. Zutterman, "TDDFT investigation of the optical properties of cyanine dyes", Chem. Phys. Lett., 425, 105-109, 2006.#42.D. Jacquemin, M. Bouhy, E. A. Perpe`te, "Excitation spectra of nitro-diphenylaniline: accurate time-dependent density functional theory predictions for charge-transfer dyes", J. Chem. Phys., 124, 204321, 2006.#43.K. Okuno, Y. Shigeta, R. Kishi, M. Nakano, "Non-empirical tuning of CAM-B3LYP functional in time-dependent density functional theory for excitation energies of diarylethene derivatives", Chem. Phys. Lett., 585, 201-206, 2013.#44.M. B. Tsinberg, S. Y. Lew, J. D. Gough, "Analysis of indolylfulgide spectral properties using time dependent density functional theory", J. Lumin., 132, 1929-1934, 2012.#45.S.-I. Lu, "The K-band ?max values of the ultraviolet–visible spectra of some hydrazones in ethanol by a TD-DFT/PCM approach", Chem. Phys. Lett., 494, 198-201, 2010.#46.D. Jacquemin, J. Preat, V. Wathelet, M. Fontaine, E. A. Perpe`te, "Thioindigo dyes: highly accurate visible spectra with TD-DFT", J. Am. Chem. soc., 128, 2072-2083, 2006.#47.D. Jacquemin, J. Preat, V. Wathelet, E. A. Perpe`te, "Time-dependent density functional theory determination of the absorption spectra of naphthoquinones", Chem. Phys., 328, 324-332, 2006.#48.D. Jacquemin, E. A. Perpe`te, "The n ? ?* transition in nitroso compounds: A TD-DFT study", Chem. Phys. Lett., 420, 529–533, 2006.#49.S. Fleming, A. Mills, T. Tuttle, "Predicting the UV–vis spectra of oxazine dyes", Beilstein J. Org. Chem., 7, 432-441, 2011.#50.I. Infante, F. Lelj, "Role of methyl substitution on the spectroscopic properties of porphyrazines. A TDDFT study using pure and hybrid functionals on porphyrazine and its octamethyl derivative", Chem. Phys. Lett., 367, 308-318, 2003.#51.E. H. Anouar, J. Gierschner, J.-L. Duroux, P. Trouillas, "UV/Visible spectra of natural polyphenols: A time-dependent density functional theory study", Food Chem., 131, 79-89, 2012.#52.M. P. Balanay, D. H. Kim, "DFT/TD-DFT molecular design of porphyrin analogues for use in dye-sensitized solar cells", Phys. Chem. Chem. Phys., 10, 5121-5127, 2008.#53.A. G. Crawford, A. D. Dwyer, Z. Liu, A. Steffen, A. Beeby, L.-O. P?lsson, D. J. Tozer, T. B. Marder, "Experimental and theoretical studies of the photophysical properties of 2- and 2, 7-functionalized pyrene derivatives", J. Am. Chem. Soc., 133, 13349-13362, 2011.#54.D. Jacquemin, A. Lewalle, E. A. Perpe`te, "Modelling the acidochromism of pyridylazulenes", Chem. Phys. Lett., 457, 91-95, 2008.#55.A. Perrier, F. Maurel, E. A. Perpe`te, V. Wathelet, D. Jacquemin, "Spectral Properties of Spirooxazine Photochromes: TD-DFT Insights", J. Phys. Chem. A, 113, 13004-13012, 2009.#56.D. Jacquemin, V. Wathelet, E. A. Perpe`te, "Ab Initio Investigation of the n ? ?* Transitions in Thiocarbonyl Dyes", J. Phys. Chem. A, 110, 9145-9152, 2006.#57.D. Jacquemin, J. Preat, V. Wathelet, M. Fontaine, E. A. Perpe`te, "Thioindigo Dyes: Highly Accurate Visible Spectra with TD-DFT", J. Am. Chem. Soc., 128, 2072-2083, 2006.#58.J. Preat, C. Michaux, A. Lewalle, E. A. Perpe`te, D. Jacquemin, "Delocalisation in conjugated triazene chromophores: Insights from theory", Chem. Phys. Lett., 451, 37-42, 2008.#59.J. Preat, D. Jacquemin, C. Michaux, E. Perpe`te, "Improvement of the efficiency of thiophene-bridged compounds for dye-sensitized solar cells", Chem. Phys., 376, 56-68, 2010.#60.J. Preat, V. Wathelet, J. M. Andre´, D. Jacquemin, E. A. Perpe`te, "Towards the understanding of the chromatic behaviour of triphenylmethane derivatives", Chem. Phys., 335, 177-186, 2007.#



فایل مقاله
تعداد بازدید: 8351
تعداد دریافت فایل مقاله : 65