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New Design Strategies for the Prepar...

Du, Yachu,

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New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons /

Record Type:	Electronic resources : Monograph/item
Title/Author:	New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons // Yachu Du.
Author:	Du, Yachu,
Description:	1 electronic resource (95 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 83-01, Section: B.
Contained By:	Dissertations Abstracts International83-01B.
Subject:	Chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28412292
ISBN:	9798516932038

New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons /
Du, Yachu,

New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons /Yachu Du. - 1 electronic resource (95 pages)

Source: Dissertations Abstracts International, Volume: 83-01, Section: B.

In this contribution, we demonstrate a new strategy to build electron deficient centers and electron accepting compounds through fusion of cyclopentene units. Two series of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs) were designed and synthesized as possible n-type semiconductors. One series of CP-PAHs were prepared by a palladium catalyzed cyclopentannulation reaction from precursors derived from the low-cost dye Vat Orange 3 (4,10-dibromoanthanthrone). The new cyclopenta-anthanthrene compounds possessed reduced optical and electrochemical gaps compared to anthanthrene derivatives and were electron acceptors with lowest unoccupied molecular orbital energies of ~ -3.4 eV to -3.9 eV. In a second research direction, CP-PAH chromophores were linked through two five-membered rings to create a new semiconductor linkage strategy. We show this new linker design can access planarized structures with reduced optical gaps and redox potentials. Two aceanthrylene chromophores were connected into dimer model systems with the chromophores either projected outward (2,2'-biaceanthrylene) or inward (1,1'-biaceanthrylene) and the optical and electronic properties were compared. Only the planar 2,2'-biaceanthrylene system showed significant reductions of the optical gaps (1 eV) and redox potentials in relation to the aceanthrylene monomer.

English

ISBN: 9798516932038Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

Acceptor

New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons /
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100 1 $a Du, Yachu, $e author. $3 3765672
245 1 0 $a New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons / $c Yachu Du.
264 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2021
300 $a 1 electronic resource (95 pages)
336 $a text $b txt $2 rdacontent
337 $a computer $b c $2 rdamedia
338 $a online resource $b cr $2 rdacarrier
500 $a Source: Dissertations Abstracts International, Volume: 83-01, Section: B.
500 $a Advisors: Plunkett, Kyle Committee members: Gao, Yong; Hou, Yuqing ; Mondal, Kanchan; Wang, Lichang.
502 $b Ph.D. $c Southern Illinois University at Carbondale $d 2021.
520 $a In this contribution, we demonstrate a new strategy to build electron deficient centers and electron accepting compounds through fusion of cyclopentene units. Two series of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs) were designed and synthesized as possible n-type semiconductors. One series of CP-PAHs were prepared by a palladium catalyzed cyclopentannulation reaction from precursors derived from the low-cost dye Vat Orange 3 (4,10-dibromoanthanthrone). The new cyclopenta-anthanthrene compounds possessed reduced optical and electrochemical gaps compared to anthanthrene derivatives and were electron acceptors with lowest unoccupied molecular orbital energies of ~ -3.4 eV to -3.9 eV. In a second research direction, CP-PAH chromophores were linked through two five-membered rings to create a new semiconductor linkage strategy. We show this new linker design can access planarized structures with reduced optical gaps and redox potentials. Two aceanthrylene chromophores were connected into dimer model systems with the chromophores either projected outward (2,2'-biaceanthrylene) or inward (1,1'-biaceanthrylene) and the optical and electronic properties were compared. Only the planar 2,2'-biaceanthrylene system showed significant reductions of the optical gaps (1 eV) and redox potentials in relation to the aceanthrylene monomer.
546 $a English
590 $a School code: 0209
650 4 $a Chemistry. $3 516420
650 4 $a Organic chemistry. $3 523952
653 $a Acceptor
653 $a Organic semiconductor
690 $a 0485
690 $a 0490
710 2 $a Southern Illinois University at Carbondale. $b Chemistry. $e degree granting institution. $3 3765673
720 1 $a Plunkett, Kyle $e degree supervisor.
773 0 $t Dissertations Abstracts International $g 83-01B.
790 $a 0209
791 $a Ph.D.
792 $a 2021
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28412292