Thieno[3,2-b]pyrrolo donor fused with benzothiadiazolo, benzoselenadiazolo and quinoxalino acceptors: Synthesis, characterization, and molecular properties

Yen-Ju Cheng; Chiu Hsiang Chen; Yu Ju Ho; Shu Wei Chang; Henryk Arnold Witek; Chain-Shu Hsu

doi:10.1021/ol202199v

Thieno[3,2-b]pyrrolo donor fused with benzothiadiazolo, benzoselenadiazolo and quinoxalino acceptors: Synthesis, characterization, and molecular properties

Yen-Ju Cheng^*, Chiu Hsiang Chen, Yu Ju Ho, Shu Wei Chang, Henryk Arnold Witek, Chain-Shu Hsu

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

Abstract

Nitrogen-bridged donor-acceptor multifused dithienopyrrolobenzothiadiazole (DTPBT) and dibenzothiadiazolopyrrolothiophene (DBTPT) were successfully synthesized by intramolecular Cadogan annulation. The electron-deficient benzothiadiazole unit in DTPBT can be converted to benzoselenadiazole and quinoxaline moieties through reduction/cyclization to generate dithienopyrrolobenzoselenadiazole (DTPBSe) and dithienopyrroloquinoxaline (DTPQX), respectively. The nitrogen atoms function as the bridges for covalent planarization to induce intermolecular interaction and intramolecular charge transfer.

Original language	English
Pages (from-to)	5484-5487
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	20
DOIs	https://doi.org/10.1021/ol202199v
State	Published - 21 Oct 2011

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title = "Thieno[3,2-b]pyrrolo donor fused with benzothiadiazolo, benzoselenadiazolo and quinoxalino acceptors: Synthesis, characterization, and molecular properties",

abstract = "Nitrogen-bridged donor-acceptor multifused dithienopyrrolobenzothiadiazole (DTPBT) and dibenzothiadiazolopyrrolothiophene (DBTPT) were successfully synthesized by intramolecular Cadogan annulation. The electron-deficient benzothiadiazole unit in DTPBT can be converted to benzoselenadiazole and quinoxaline moieties through reduction/cyclization to generate dithienopyrrolobenzoselenadiazole (DTPBSe) and dithienopyrroloquinoxaline (DTPQX), respectively. The nitrogen atoms function as the bridges for covalent planarization to induce intermolecular interaction and intramolecular charge transfer.",

author = "Yen-Ju Cheng and Chen, {Chiu Hsiang} and Ho, {Yu Ju} and Chang, {Shu Wei} and Witek, {Henryk Arnold} and Chain-Shu Hsu",

year = "2011",

month = oct,

day = "21",

doi = "10.1021/ol202199v",

language = "English",

volume = "13",

pages = "5484--5487",

journal = "Organic Letters",

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T1 - Thieno[3,2-b]pyrrolo donor fused with benzothiadiazolo, benzoselenadiazolo and quinoxalino acceptors

T2 - Synthesis, characterization, and molecular properties

AU - Cheng, Yen-Ju

AU - Chen, Chiu Hsiang

AU - Ho, Yu Ju

AU - Chang, Shu Wei

AU - Witek, Henryk Arnold

AU - Hsu, Chain-Shu

PY - 2011/10/21

Y1 - 2011/10/21

N2 - Nitrogen-bridged donor-acceptor multifused dithienopyrrolobenzothiadiazole (DTPBT) and dibenzothiadiazolopyrrolothiophene (DBTPT) were successfully synthesized by intramolecular Cadogan annulation. The electron-deficient benzothiadiazole unit in DTPBT can be converted to benzoselenadiazole and quinoxaline moieties through reduction/cyclization to generate dithienopyrrolobenzoselenadiazole (DTPBSe) and dithienopyrroloquinoxaline (DTPQX), respectively. The nitrogen atoms function as the bridges for covalent planarization to induce intermolecular interaction and intramolecular charge transfer.

AB - Nitrogen-bridged donor-acceptor multifused dithienopyrrolobenzothiadiazole (DTPBT) and dibenzothiadiazolopyrrolothiophene (DBTPT) were successfully synthesized by intramolecular Cadogan annulation. The electron-deficient benzothiadiazole unit in DTPBT can be converted to benzoselenadiazole and quinoxaline moieties through reduction/cyclization to generate dithienopyrrolobenzoselenadiazole (DTPBSe) and dithienopyrroloquinoxaline (DTPQX), respectively. The nitrogen atoms function as the bridges for covalent planarization to induce intermolecular interaction and intramolecular charge transfer.

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U2 - 10.1021/ol202199v

DO - 10.1021/ol202199v

M3 - Article

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JO - Organic Letters

JF - Organic Letters

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ER -

Thieno[3,2-b]pyrrolo donor fused with benzothiadiazolo, benzoselenadiazolo and quinoxalino acceptors: Synthesis, characterization, and molecular properties

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