Presentation Title

Novel Synthesis of Triflate-Substituted [1]Benzothieno[3,2-b][1]benzothiophene Compounds and Further Functionalization

Presenter's Name(s)

Brian M. CovenFollow

Project Collaborators

Dr. Adam Whalley (faculty mentor), Adam Dyer (graduate student mentor)

Abstract

Alternatives to energy-expensive and inflexible silicon-based semiconductors have long been sought after through extensive exploration of organic semiconductors. While these compounds will never replicate the amazing properties of inorganic semiconductors, they exhibit many properties that are advantageous over their inorganic counterparts. For example, these organic semiconductors are highly soluble in common organic solvents allowing for large area processing, and methodology to synthesize derivatives allows for targeted adjustment of the properties of the compounds. [1]benzothieno[3,2-b][1]benzothiophene (BTBT) is one of the best known organic semiconductors. However, there are currently no adequate methods to add diverse functionality to its core structure, thereby limiting its potential. This project will explore the synthesis and application of a triflate-functionalized BTBT derivative, which will allow for late-stage installation of functional groups, fine-tuning of the electronic properties, and molecular packing in thin films in a diverse family of derivatives. Crystal structure of reaction products will be observed along with the electronic properties of successfully synthesized BTBT derivatives.

Primary Faculty Mentor Name

Adam Whalley

Graduate Student Mentors

Adam Dyer

Status

Undergraduate

Student College

College of Arts and Sciences

Program/Major

Biochemistry

Primary Research Category

Engineering & Physical Sciences

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Novel Synthesis of Triflate-Substituted [1]Benzothieno[3,2-b][1]benzothiophene Compounds and Further Functionalization

Alternatives to energy-expensive and inflexible silicon-based semiconductors have long been sought after through extensive exploration of organic semiconductors. While these compounds will never replicate the amazing properties of inorganic semiconductors, they exhibit many properties that are advantageous over their inorganic counterparts. For example, these organic semiconductors are highly soluble in common organic solvents allowing for large area processing, and methodology to synthesize derivatives allows for targeted adjustment of the properties of the compounds. [1]benzothieno[3,2-b][1]benzothiophene (BTBT) is one of the best known organic semiconductors. However, there are currently no adequate methods to add diverse functionality to its core structure, thereby limiting its potential. This project will explore the synthesis and application of a triflate-functionalized BTBT derivative, which will allow for late-stage installation of functional groups, fine-tuning of the electronic properties, and molecular packing in thin films in a diverse family of derivatives. Crystal structure of reaction products will be observed along with the electronic properties of successfully synthesized BTBT derivatives.