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Carbazole Based Ambipolar Compounds: A Study of Their Intramolecular Charge Transfer Properties

Estrada, Leandro A.
http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1282247858

Abstract Details

2010, Doctor of Philosophy (Ph.D.), Bowling Green State University, Photochemical Sciences.
The present manuscript describes the synthesis and photophysical properties of six carbazole-based ambipolar compounds with donor-acceptor-donor (hereafter D-A-D) configuration in C2v symmetric arrangement. Three acceptor units were chosen based on their known optical properties, symmetry and planarity: fluorenone (FO), fluoren-9-ylidene malononitrile (FM), and dibenz[a,c]phenazine (Pz). Such units were connected through a phenylacetylene (PA) bridge (B) to favor structural rigidity and keep D-A distances fairly constant. The acceptor unit was functionalized through their common biphenylene skeleton via 3,3' and 4,4' substitutions (in the manuscript they adopt the numerology from fluorene). The triads B-A-B were also synthesized for comparison purposes. The photophysical properties have been investigated by means of steady state and time resolved UV-Vis absorption and photoluminescence, plus cyclic voltammetry. Computational methods such as density functional theory (DFT) and post self-consistent field (SCF) (i.e. complete active space SCF, or CASSCF) were utilized to map the electronic properties of the derivatives and perform a first survey of the possible non-radiative relaxation mechanism of their S1 state. The focus of these studies was based on the structure-activity relationship between the pattern of substitution and the electronic properties of the bulk. This helped establishing design patterns for the next generation of chromophores to be utilized in organic electronics applications such as thin-film transistors and photovoltaics, based on these D and A units.
Douglas Neckers, PhD (Advisor)
Massimo Olivucci, PhD (Committee Co-Chair)
Marshall Wilson, PhD (Committee Member)
Felix Castellano, PhD (Committee Member)
Lee Meserve, PhD (Other)
332 p.
Chemistry
CARBAZOLE; AMBIPOLAR COMPOUNDS; CHARGE TRANSFER; FLUORENONE

Recommended Citations

Citations

  • Estrada, L. A. (2010). Carbazole Based Ambipolar Compounds: A Study of Their Intramolecular Charge Transfer Properties [Doctoral dissertation, Bowling Green State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1282247858

    APA Style (7th edition)

  • Estrada, Leandro. Carbazole Based Ambipolar Compounds: A Study of Their Intramolecular Charge Transfer Properties. 2010. Bowling Green State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1282247858.

    MLA Style (8th edition)

  • Estrada, Leandro. "Carbazole Based Ambipolar Compounds: A Study of Their Intramolecular Charge Transfer Properties." Doctoral dissertation, Bowling Green State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1282247858

    Chicago Manual of Style (17th edition)

bgsu1282247858
409
© 2010, all rights reserved.
This open access ETD is published by Bowling Green State University and OhioLINK.