Presentation Title

Unlocking the electronic genome of halogeno-naphthalene/anthracene

Faculty Mentor

Bohdan Schatschneider

Start Date

18-11-2017 9:59 AM

End Date

18-11-2017 11:00 AM

Location

BSC-Ursa Minor 133

Session

Poster 1

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

The search for stable, cheap organic materials for use in optoelectronic devices has led to the exploration of the electronic properties of functionalized polycyclic aromatic hydrocarbons (PAHs). In this study, high-throughput density functional theory (DFT) is used to explore the effect homogenous halogenation has on the HOMO-LUMO gaps of naphthalene and anthracene derivatives, and the physicochemical trends that emerge with respect to substituent position, polarizability, and aromaticity. It is shown that substituent position and polarizability are the primary factors controlling the HOMO-LUMO gap (EgH-L) as these properties control the aromaticity (calculated via the harmonic oscillator method of aromaticity index [HOMA]) and HOMO/LUMO energies. Interesting trends in the HOMO-LUMO gap as a function of HOMA are analyzed and presented in-depth. Specifically, the chlro-, bromo-, and iodo-naphthalene/anthracene structures cluster into three “EgH-L-HOMA regions” (region A, region B, and region C), while fluoro- structures are all clustered together. It has also been determined that iodine containing structures have the smallest EgH-L's, however they are least stable according to their low HOMA indices. In region A, iodo-structures have EgH-L's as low as 0.72 eV but HOMA values of values of <0.55. Chloro- and bromo-structures in region B have HOMA values of 0.68-0.73 and 0.65-0.72 with EgH-L's of 2.71-2.99 eV and 2.62-2.91 eV, respectively. Ultimately, the purpose of this study is to computationally model the electronic properties of these halogenonaphthalenes in order to rapidly identify suitable candidates for synthesis. Therefore, bromo-structures should be selected.

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Nov 18th, 9:59 AM Nov 18th, 11:00 AM

Unlocking the electronic genome of halogeno-naphthalene/anthracene

BSC-Ursa Minor 133

The search for stable, cheap organic materials for use in optoelectronic devices has led to the exploration of the electronic properties of functionalized polycyclic aromatic hydrocarbons (PAHs). In this study, high-throughput density functional theory (DFT) is used to explore the effect homogenous halogenation has on the HOMO-LUMO gaps of naphthalene and anthracene derivatives, and the physicochemical trends that emerge with respect to substituent position, polarizability, and aromaticity. It is shown that substituent position and polarizability are the primary factors controlling the HOMO-LUMO gap (EgH-L) as these properties control the aromaticity (calculated via the harmonic oscillator method of aromaticity index [HOMA]) and HOMO/LUMO energies. Interesting trends in the HOMO-LUMO gap as a function of HOMA are analyzed and presented in-depth. Specifically, the chlro-, bromo-, and iodo-naphthalene/anthracene structures cluster into three “EgH-L-HOMA regions” (region A, region B, and region C), while fluoro- structures are all clustered together. It has also been determined that iodine containing structures have the smallest EgH-L's, however they are least stable according to their low HOMA indices. In region A, iodo-structures have EgH-L's as low as 0.72 eV but HOMA values of values of <0.55. Chloro- and bromo-structures in region B have HOMA values of 0.68-0.73 and 0.65-0.72 with EgH-L's of 2.71-2.99 eV and 2.62-2.91 eV, respectively. Ultimately, the purpose of this study is to computationally model the electronic properties of these halogenonaphthalenes in order to rapidly identify suitable candidates for synthesis. Therefore, bromo-structures should be selected.