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You searched for subject:(direct borylation). Showing records 1 – 3 of 3 total matches.

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Boston College

1. Eliseeva, Maria N. New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene.

Degree: MS, Chemistry, 2011, Boston College

The Scott lab is interested in the functionalization of corannulene as a building block for large polycyclic aromatic hydrocarbons and carbon nanotube end-cap precursors. Toward that end, a new approach to the direct five-fold borylation of corannulene with iridium (I) catalysts via C-H activation has been explored. It has been discovered that the addition of catalytic amounts of base to the reaction mixture promotes the formation of symmetrical penta-borylated corannulene in a good yield on a sizable scale. All byproducts can be easily removed with iterative methanol washes. The present work also provides proof of the reversibility of the direct borylation reaction under the conditions used. Furthermore, modified Suzuki-Miyaura conditions have been employed to synthesize pentakis(2,6-dichlorophenyl)corannulene, a precursor for a [5,5] carbon nanotube end-cap. The reported reactions provide good yields and are scalable. Advisors/Committee Members: Lawrence T. Scott (Thesis advisor).

Subjects/Keywords: carbon nanotube; corannulene; direct borylation; iridium catalyst; Suzuki reaction

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Eliseeva, M. N. (2011). New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene. (Masters Thesis). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101796

Chicago Manual of Style (16th Edition):

Eliseeva, Maria N. “New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene.” 2011. Masters Thesis, Boston College. Accessed October 22, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101796.

MLA Handbook (7th Edition):

Eliseeva, Maria N. “New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene.” 2011. Web. 22 Oct 2019.

Vancouver:

Eliseeva MN. New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene. [Internet] [Masters thesis]. Boston College; 2011. [cited 2019 Oct 22]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101796.

Council of Science Editors:

Eliseeva MN. New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene. [Masters Thesis]. Boston College; 2011. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101796


University of Manchester

2. Crossley, Daniel. Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers.

Degree: 2016, University of Manchester

The synthesis, photophysical and electronic properties of a series of novel boron containing fused and ladder type donor−acceptor (D-A) oligomers and polymers are reported. The synthesis was achieved through coordination of the basic functionality of the ubiquitous benzothiadiazole acceptor unit onto a boron Lewis acid followed by an electrophilic aromatic borylation resulting in the formation of fused and ladder type structures (termed borylative fusion). The novel C,N-chelated borane structures disclosed herein are a new member of a large family of tetra-coordinate organoboron compounds that are used for the construction of highly emissive materials. Upon borylation large bathochromic shifts in the absorption and fluorescence spectra were observed, DFT and cyclic voltammetry demonstrate that this is a result of a significant reduction of the LUMO energy levels whist the HOMO energy levels remains relatively unperturbed. These large bathochromic shifts lead to materials that show far red/NIR emission in the solid state with absolute quantum yields of up to 44%. Furthermore, the frontier molecular orbital energy levels of these fused structures can be modulated through judicious selection of the exocyclic boron substituents. These novel borocycles also proved stable to a range of cross-coupling conditions which facilitated further modulation of the frontier molecular orbitals and emissive properties. Borylative fusion was also applicable to D-A conjugated polymers, this represents a facile post-polymerisation functionalisation that is an effective method of modulating the photophysical properties of D-A conjugated polymers. Solution processed OLEDs with far red/NIR electroluminescence (EL) were fabricated from these materials. These devices showed good external quantum efficiency values (EQE) for the far red/NIR region of the electromagnetic spectrum (EQE >0.4 % for maximum EL >700 nm).

This thesis describes the synthesis and photophysical properties of tetra-coordinate C,N-chelated donor-acceptor organoboron compounds.

Advisors/Committee Members: TURNER, MICHAEL ML, Turner, Michael, Ingleson, Michael.

Subjects/Keywords: Boron; Donor-Acceptor Compounds; OLEDs; Polymers; Near Infra-red Emission; Organoboron; Direct C-H Electrophilic Borylation

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Crossley, D. (2016). Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers. (Doctoral Dissertation). University of Manchester. Retrieved from http://www.manchester.ac.uk/escholar/uk-ac-man-scw:301616

Chicago Manual of Style (16th Edition):

Crossley, Daniel. “Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers.” 2016. Doctoral Dissertation, University of Manchester. Accessed October 22, 2019. http://www.manchester.ac.uk/escholar/uk-ac-man-scw:301616.

MLA Handbook (7th Edition):

Crossley, Daniel. “Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers.” 2016. Web. 22 Oct 2019.

Vancouver:

Crossley D. Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers. [Internet] [Doctoral dissertation]. University of Manchester; 2016. [cited 2019 Oct 22]. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:301616.

Council of Science Editors:

Crossley D. Directed C-H Borylation for the Synthesis of Fused and Ladder Type Conjugated Oligomers and Polymers. [Doctoral Dissertation]. University of Manchester; 2016. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:301616


University of Manchester

3. Crossley, Daniel. Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers.

Degree: PhD, 2016, University of Manchester

The synthesis, photophysical and electronic properties of a series of novel boron containing fused and ladder type donor-acceptor (D-A) oligomers and polymers are reported. The synthesis was achieved through coordination of the basic functionality of the ubiquitous benzothiadiazole acceptor unit onto a boron Lewis acid followed by an electrophilic aromatic borylation resulting in the formation of fused and ladder type structures (termed borylative fusion). The novel C,N-chelated borane structures disclosed herein are a new member of a large family of tetra-coordinate organoboron compounds that are used for the construction of highly emissive materials. Upon borylation large bathochromic shifts in the absorption and fluorescence spectra were observed, DFT and cyclic voltammetry demonstrate that this is a result of a significant reduction of the LUMO energy levels whist the HOMO energy levels remains relatively unperturbed. These large bathochromic shifts lead to materials that show far red/NIR emission in the solid state with absolute quantum yields of up to 44%. Furthermore, the frontier molecular orbital energy levels of these fused structures can be modulated through judicious selection of the exocyclic boron substituents. These novel borocycles also proved stable to a range of cross-coupling conditions which facilitated further modulation of the frontier molecular orbitals and emissive properties. Borylative fusion was also applicable to D-A conjugated polymers, this represents a facile post-polymerisation functionalisation that is an effective method of modulating the photophysical properties of D-A conjugated polymers. Solution processed OLEDs with far red/NIR electroluminescence (EL) were fabricated from these materials. These devices showed good external quantum efficiency values (EQE) for the far red/NIR region of the electromagnetic spectrum (EQE > 0.4 % for maximum EL > 700 nm).

Subjects/Keywords: 540; Organoboron; Direct C-H Electrophilic Borylation; Near Infra-red Emission; Boron; OLEDs; Donor-Acceptor Compounds; Polymers

Record DetailsSimilar RecordsGoogle PlusoneFacebookTwitterCiteULikeMendeleyreddit

APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Crossley, D. (2016). Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers. (Doctoral Dissertation). University of Manchester. Retrieved from https://www.research.manchester.ac.uk/portal/en/theses/directed-ch-borylation-for-the-synthesis-of-fused-and-ladder-type-conjugated-oligomers-and-polymers(8c96a89b-7442-41f3-839b-56148b5fd458).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.748012

Chicago Manual of Style (16th Edition):

Crossley, Daniel. “Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers.” 2016. Doctoral Dissertation, University of Manchester. Accessed October 22, 2019. https://www.research.manchester.ac.uk/portal/en/theses/directed-ch-borylation-for-the-synthesis-of-fused-and-ladder-type-conjugated-oligomers-and-polymers(8c96a89b-7442-41f3-839b-56148b5fd458).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.748012.

MLA Handbook (7th Edition):

Crossley, Daniel. “Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers.” 2016. Web. 22 Oct 2019.

Vancouver:

Crossley D. Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers. [Internet] [Doctoral dissertation]. University of Manchester; 2016. [cited 2019 Oct 22]. Available from: https://www.research.manchester.ac.uk/portal/en/theses/directed-ch-borylation-for-the-synthesis-of-fused-and-ladder-type-conjugated-oligomers-and-polymers(8c96a89b-7442-41f3-839b-56148b5fd458).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.748012.

Council of Science Editors:

Crossley D. Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers. [Doctoral Dissertation]. University of Manchester; 2016. Available from: https://www.research.manchester.ac.uk/portal/en/theses/directed-ch-borylation-for-the-synthesis-of-fused-and-ladder-type-conjugated-oligomers-and-polymers(8c96a89b-7442-41f3-839b-56148b5fd458).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.748012

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