Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures
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The Ohio State University / OhioLINK
2015
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ndltd-OhioLink-oai-etd.ohiolink.edu-osu14290394682021-08-03T06:30:02Z Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures Sanchez, Daniel Antonio Chemistry The following are reported studies of non-covalent interactions that have been utilized to construct complex self-assembled materials. An l-lysine based amphiphile that contains a p-conjugated chromophore with a polymerizable diacetylene unit has been synthesized and assembled into a 1D nanostructure. Various 1D nanostructures have been reported in the literature, but few have the ability to polymerize. Not only does this improve the stability of the nanostructure, but it also allows for post polymerization functionalization. Therefore, the design and synthesis of nanostructures with added complexity can be developed. The design of the amphiphile consists of L-lysine derivatives functionalized at the terminus, naphthalene diimide (NDI), an n-butyl tail, and a diacetylene unit that is capable of polymerization. The self-assembly of this system is driven by hydrophobic/hydrophilic interactions of the polar head and n-butyl tail. In addition, p-p interactions of NDI core add an extra form of stabilization to the molecule. Polymerization was initiated by use of a 254 nm UV lamp on the self-assembled system. UV absorbance spectroscopy results showed that cross-linked occurred readily by monitoring the absorbance centered at 593 nm. The results demonstrated that the polymerization of the self-assembled semiconducting nanostructure has an increased stability to pH, elevated temperature, and solvent change. Whereas hydrolysis, high temperature, and solvent change all lead to the decomposition of the cross-linked nanostructure. There has been much interest in the development of electronic devices that contain an organic semiconducting film due to the low production cost, lightweight structure and flexible properties. Several variations of organic donor acceptor arrays have been created in resemblance of bulk heterojunctions, which should exhibit have efficient charge separation. Therefore, incorporating a polymerizable unit into a dyad system not only provides enhanced stability, but also increases p-conjugation. The design of the dyad amphiphile consists of an L-lysine amino acid, naphthalene diimide, tetraphenylporphyrin (TPP) and a diacetylene unit. Preliminary results show that this dyad system self-assembles into a nanostructure that is polymerizable in THF. The structure went from a non-directional (2D) structure to a directional (1D) structure upon irritation. Indicating that a second non-covalent interaction, hydrogen bonding, changed the assembly. Unfortunately, a non-uniform structure is formed and seen in TEM images. Nonetheless, this self assembled compound participated in FRET, meaning it was able to electron transfer between NDI and porphyrin chromophores. 2015-05-21 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1429039468 http://rave.ohiolink.edu/etdc/view?acc_num=osu1429039468 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
| collection |
NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry |
| spellingShingle |
Chemistry Sanchez, Daniel Antonio Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| author |
Sanchez, Daniel Antonio |
| author_facet |
Sanchez, Daniel Antonio |
| author_sort |
Sanchez, Daniel Antonio |
| title |
Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| title_short |
Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| title_full |
Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| title_fullStr |
Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| title_full_unstemmed |
Amphiphilic Self-Assembly & Post-Polymerization of N-type Conjugated Optoelectronic Nanostructures |
| title_sort |
amphiphilic self-assembly & post-polymerization of n-type conjugated optoelectronic nanostructures |
| publisher |
The Ohio State University / OhioLINK |
| publishDate |
2015 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=osu1429039468 |
| work_keys_str_mv |
AT sanchezdanielantonio amphiphilicselfassemblypostpolymerizationofntypeconjugatedoptoelectronicnanostructures |
| _version_ |
1719437911895572480 |