Conclusion

Synthesis of Dibenzo(b,f)(1,5)diazocine-6,12(5H,11H)-dione

Chameleon 2 Compound Hiram Castillo-Marquez1, Ziwei Pan2, Tomas Espinoza3, Saideh Mortazavi3, James Salvador3

El Paso Community College1, Beijing Normal University2, University of Texas at El Paso3

Many people around the world are experiencing Computer Vision Syndrome (CVS) which leads to eyestrain, headaches, blurred vision, dry eyes, neck-shoulder pain and, overtime, vision loss. Devices such as tablets and smartphones require batteries that function longer. With an increase demand on battery improvement, but at the same time an increase in sight deficiency due to screens, new technologies that can address these two problems are needed.

Student Research was supported in part by the National Institute of General Medical Sciences of the National Institutes of Health under RISE Award Number R25GM060424. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health.

Future Endeavors

Methodology

Results

Objectives

Introduction

Acknowledgements

Combining the concepts of conjugation and aromaticity, we propose to synthesize and characterize bent non-aromatic compounds (no absorption in the visible spectrum) that can be converted electronically to flat more conjugated aromatic compounds (absorption in the visible spectrum)(Experiment 1.1) and vice versa.

• The NMR of the precipitate shows that it is the starting compound.

• The spectrum showed that the compound absorbs ultra-violet but not much visible light.

• Dibenzo(b,f)(1,5)diazocine-6,12(5H,11H) was synthesized from phthalic acid in five steps in an overall 13 % yield.

• Upon refluxing this compound in THF it dissolved. Adding lithium metal caused the solution to get cloudy. We believe this compound is the dianion of the title compound.

1. Add benzene rings to both sides of the basic structure to get more conjugate molecules that absorb light in the visible spectrum.

2. Synthesize at least three molecules that can cover the color palette, i.e., red, green and blue dyes.

3. Electronically manipulate color change rather than using metals.

2K-2

• Step 3: Methyl 2-AminoBenzoate was dissolved in tetrahydrofuran (THF) in an ice

bath (Picture 1.1), and reacted with sodium hydride to form dibenzo(b,f)(1,5)diazocine-6,12(5H,11H)-dione (Figure 1.6)(Picture 1.2 & Picture 1.3).

• Step 4: Dibenzo(b,f)(1,5)diazocine-6,12(5H,11H)-dione (Chameleon 2) was dissolved in THF, lithium was added (Figure 1.7)(Picture 1.4), and the reaction was refluxed overnight. The resulting suspension was monitored by UV-Visible spectroscopy.

35% from phthalic acid 45 % from phthalamic acid

84%

Step 1 Step 2 Step 3

Step 4

Chameleon 2

References

Figure 1.1 Figure 1.2 Figure 1.3 Figure 1.4 Figure 1.5 Figure 1.6

Figure 1.7

Picture 1.1 Picture 1.2 Picture 1.3 Picture 1.4

Gra

ph

1.1

Gra

ph

1.2

. Most electronic devices use emission sources which cause CVS symptoms and consume a significant amount of energy, but using absorption displays we can

reduce CVS symptoms and consume less energy.

Jellyfish’s (right side) movement resembles the molecules’ movement in

an aromatic compound. Spanish dancer’s (left side) movement resembles

the molecules’ movement in a non-aromatic compound

Experiment 1.1

1.Comiskey, Albert; Yoshizawa, Jacobson Nature 1998, 394, (6690). 2.Paudler and Zeiler, Journal of Organic Chemistry, 1968, 2138. 3.Bill and Tarbell, Organic Syntheses, Coll. Vol. 4, p.807 (1963); Vol. 34, p.82 (1954). 4.Carlson, Srinivasachar, Givens and Matuszewski , Journal of Organic Chemistry, 1986, 3979. 5.Skoog and West, Principles of Instrumental Analysis, 2nd ed.

Octatetraene can change color by adding electrons, but it only happens in the UV spectrum.

Methodology • Step 1: Phthalic acid (Figure 1.1) was refluxed in thionyl

chloride to convert it into phthalic anhydride (Figure 1.2) and reacted with ammonium hydroxide to form phthalamic acid (Figure 1.3).

• Step 2: Phthalamic acid was reacted with cooled 8 %

sodium hypochlorite solution (concentrated bleach) and sodium hydroxide to form anthranilic acid (2-aminobenzoic acid) (Figure 1.4) via the Beckmann rearrangement reaction. After acidifying and cool down, thionyl chloride and methanol were added and the mixture was refluxed to form methyl 2-aminobenzoate (Figure 1.5).

The left side is non-aromatic and lesser conjugated. The right side is aromatic and more conjugated meaning it absorbs more light.

The basic solution (Picture 1.1) was collected, and acidify to get the chameleon 2 compound (Picture 1.2).

Conclusion • The UV-Visible spectrum of the supposed dianion showed decreased absorption

of light over time (Graph 1.1 & Graph 1.2) with increased precipitation upon exposure to air.