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Colorful Azulene and Its Equally Colorful Derivatives
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Abstract
A simple pictorial method using HOMO, LUMO, and LUMO+1 of azulene coupled with interaction between the electrons in the singly occupied orbitals is introduced to show how the S2-S0 energy gap relative to the S1-S0 gap can be changed by a choice of substituents. The result is changing the characteristic blue color of azulene to an array of other colors: emerald green for 1,3-difluoroazulene, magenta for azulene-1-carboxaldehyde, and red for azulene-1,3-dicarboxaldehyde.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Subject):
Atomic Properties / StructureCiting Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Beyond λmax Part 2: Predicting Molecular Color
Darren L. Williams , Thomas J. Flaherty and Bassam K. AlnaslehJournal of Chemical Education2009 86 (3), 333Beyond λmax Part 2: Predicting Molecular Color
Darren L. Williams , Thomas J. Flaherty and Bassam K. AlnaslehJournal of Chemical Education2009 86 (3), 333A concise roadmap for using computational chemistry programs (i.e., Gaussian 03W) to predict the color of a molecular species is presented. A color-predicting spreadsheet is available with the online material that uses transition wavelengths and peak-...
Predicting the Shifts of Absorption Maxima of Azulene Derivatives Using Molecular Modeling and ZINDO CI Calculations of UV–Vis Spectra
Wyona C. Patalinghug , Maharlika Chang and Joanne SolisJournal of Chemical Education2007 84 (12), 1945Predicting the Shifts of Absorption Maxima of Azulene Derivatives Using Molecular Modeling and ZINDO CI Calculations of UV–Vis Spectra
Wyona C. Patalinghug , Maharlika Chang and Joanne SolisJournal of Chemical Education2007 84 (12), 1945The deep blue color of azulene is drastically changed by the addition of substituents such as CH3, F, or CHO. Computational semiempirical methods using ZINDO CI are used to model azulene and azulene derivatives and to calculate their UV–vis spectra. The ...
An Azulene-Based Discovery Experiment: Challenging Students To Watch for the "False Assumption"
Charles M. GarnerJournal of Chemical Education2005 82 (11), 1686An Azulene-Based Discovery Experiment: Challenging Students To Watch for the "False Assumption"
Charles M. GarnerJournal of Chemical Education2005 82 (11), 1686A discovery-based organic laboratory experiment designed to challenge student's assumptions is described. The students are first taught that the trifluoroacylation of azulene followed by treatment with hydroxide yields azulene-1-carboxylic acid, then are ...
"You're Repulsive!"—Teaching VSEPR in a Not-So-Elegant Way
Robert S. H. LiuJournal of Chemical Education2005 82 (4), 558"You're Repulsive!"—Teaching VSEPR in a Not-So-Elegant Way
Robert S. H. LiuJournal of Chemical Education2005 82 (4), 558Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving ...
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- Received: August 03, 2009
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