Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Template-Assisted Synthesis of Supramolecular Nanotubes, Anion Receptors, and Molecular Gloves

Mirzaei, Saber (2023) Template-Assisted Synthesis of Supramolecular Nanotubes, Anion Receptors, and Molecular Gloves. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

This is the latest version of this item.

Download (9MB) | Preview


Supramolecular chemistry has been an exciting branch of organic chemistry during the past decades. Among macrocyclic molecules, macrocyclic arenes are the most well-known and explored type of compounds. In the present thesis, I explored the chemistry of a well-known macrocyclic arene, resorcin[4]arene, as the template to synthesize contorted and strained aromatic compounds, and anion receptors. Chapter 1 provides a general introduction on supramolecular chemistry and has been divided into three sections: 1) macrocyclic molecules, 2) C–H hydrogen bonding architectures, and 3) contorted conjugated macrocycles.
In Chapter 2, I introduce our approach employing derivatized resorcin[4]arenes as templates towards the synthesis of highly strained aromatic molecules. The top rim of these molecules consists of eight para connected phenylenes and resembles the structure of [8]cyclo-para-phenylene. Chapter 3 demonstrates how the same basic template (resorcin[4]arene) can be used towards zigzag tubularenes by incorporating subtle changes in the synthetic approach. The end result is best described as radially-oriented cyclo-meta-phenylenes. The experimental and computational techniques are discussed for these novel species.
Anion recognition molecules are described in Chapter 4. Here, I demonstrate how derivatized resorcin[4]arenes form the basis to create hosts with an unprecedented ability to bind anions via C–H hydrogen bonding. The overall structure is tuned by a late-stage functionalization of the resorcin[4]arene template with a wide range of aromatic building blocks. Our novel approach demonstrates that by rigidifying and installing electron-withdrawing groups (mainly fluorine atoms), we can produce a new family of anion hosts with highly electropositive hydrogen atoms residing within the cavity of these hosts which are used to sequester non-spherical anions.
Finally, Chapter 5 presents a novel application of resorcin[4]arenes in the gram-scale synthesis of an octa-bromo cavitand, which is used in a two-step synthetic approach towards a rigid basket-like molecule that we colloquially refer to as “nanoglove”, since it is able to host or “catch” fullerenes with high affinity. In contrast to the conjugated systems reported in Chapters 2 and 3, the top rim of this molecule is made of twelve conjugated phenylenes producing an aperture suitable for fullerene binding.


Social Networking:
Share |


Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Mirzaei, Sabersam444@pitt.edusam4440000-0001-9651-9197
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairHernández Sánchez, Raúl​
Committee MemberWipt,
Committee CoChairRosi,
Committee MemberJasti,
Date: 26 January 2023
Date Type: Publication
Defense Date: 6 December 2022
Approval Date: 26 January 2023
Submission Date: 15 November 2022
Access Restriction: 1 year -- Restrict access to University of Pittsburgh for a period of 1 year.
Number of Pages: 208
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: Supramolecular chemistry Host-Guest Noncovalent Interactions
Date Deposited: 26 Jan 2023 13:49
Last Modified: 26 Jan 2024 06:15

Available Versions of this Item

  • Template-Assisted Synthesis of Supramolecular Nanotubes, Anion Receptors, and Molecular Gloves. (deposited 26 Jan 2023 13:49) [Currently Displayed]


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item