國立虎尾科技大學 |

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

紀錄類型:	書目-語言資料,手稿 : Monograph/item
正題名/作者:	New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons./
作者:	Du, Yachu.
面頁冊數:	1 online resource (95 pages)
附註:	Source: Dissertations Abstracts International, Volume: 83-01, Section: B.
Contained By:	Dissertations Abstracts International83-01B.
標題:	Organic chemistry. -
電子資源:	click for full text (PQDT)
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. - 1 online resource (95 pages)

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

Thesis (Ph.D.)--Southern Illinois University at Carbondale, 2021.

Includes bibliographical references

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.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2024

Mode of access: World Wide Web

ISBN: 9798516932038Subjects--Topical Terms:

1148722
Organic chemistry.
Subjects--Index Terms:

AcceptorIndex Terms--Genre/Form:

554714
Electronic books.

New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons.
LDR:02659ntm a22003497 4500 001 1144211
005 20240531083800.5
006 m o d
007 cr mn ---uuuuu
008 250605s2021 xx obm 000 0 eng d
020 $a 9798516932038
035 $a (MiAaPQ)AAI28412292
035 $a AAI28412292
040 $a MiAaPQ $b eng $c MiAaPQ $d NTU
100 1 $a Du, Yachu. $3 1469163
245 1 0 $a New Design Strategies for the Preparation and Linking of Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons.
264 0 $c 2021
300 $a 1 online 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 Advisor: Plunkett, Kyle.
502 $a Thesis (Ph.D.)--Southern Illinois University at Carbondale, 2021.
504 $a Includes bibliographical references
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.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2024
538 $a Mode of access: World Wide Web
650 4 $a Organic chemistry. $3 1148722
650 4 $a Chemistry. $3 593913
653 $a Acceptor
653 $a Organic semiconductor
655 7 $a Electronic books. $2 local $3 554714
690 $a 0485
690 $a 0490
710 2 $a Southern Illinois University at Carbondale. $b Chemistry. $3 1469164
710 2 $a ProQuest Information and Learning Co. $3 1178819
773 0 $t Dissertations Abstracts International $g 83-01B.
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28412292 $z click for full text (PQDT)