Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives

Armands Ruduss; Kaspars Traskovskis; Raitis Grzibovskis; Valdis Kokars

doi:10.4028/www.scientific.net/KEM.800.280

Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives

Armands Ruduss^*
, Kaspars Traskovskis
, Raitis Grzibovskis
, Valdis Kokars

^*Corresponding author for this work

Laboratory of Organic Materials, Institute of Solid State Physics

Riga Technical University

Research output: Chapter in Book/Report/Conference proceeding › Conference paper › Research › peer-review

1 Citation (Scopus)

Abstract

A modular approach was used in the synthesis of the 3-(diphenylamino)carbazolyl-functionalized 2-(4-(dimethylamino)benzylidene)-1H-indene-1,3(2H)-dione (DMABI) derivatives. For this purpose, carboxyl functional group was introduced into the framework of DMABI molecule. Additionally, a regioselective method for substitution of carbonyl group of DMABI with dicyanomethylene group was investigated and verified using the heteronuclear multiple bond correlation NMR spectra. Steglich esterification method was used to connect the 3-(diphenylamino)carbazolyl moiety via an unconjugated spacer. The UV-Vis absorption spectra and molecular energy level data were obtained for the evaluation of the synthesized compounds as donor materials in bulk-heterojunction solar cells.

Original language	English
Title of host publication	Materials Science and Applied Chemistry II
Editors	Maris Turks
Publisher	Trans Tech Publications Ltd
Pages	280-285
Number of pages	6
ISBN (Print)	9783035714074
DOIs	https://doi.org/10.4028/www.scientific.net/KEM.800.280
Publication status	Published - 2019
Event	59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry, MSAC 2018 - Riga, Latvia Duration: 26 Oct 2018 → 26 Oct 2018

Publication series

Name	Key Engineering Materials
Volume	800 KEM
ISSN (Print)	1013-9826
ISSN (Electronic)	1662-9795

Conference

Conference	59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry, MSAC 2018
Country/Territory	Latvia
City	Riga
Period	26/10/18 → 26/10/18

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

Bulk-heterojunction
Carbazole
DMABI
Organic solar cells
Regioselectivity

Access to Document

10.4028/www.scientific.net/KEM.800.280

Cite this

Ruduss, A., Traskovskis, K., Grzibovskis, R., & Kokars, V. (2019). Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives. In M. Turks (Ed.), Materials Science and Applied Chemistry II (pp. 280-285). (Key Engineering Materials; Vol. 800 KEM). Trans Tech Publications Ltd. https://doi.org/10.4028/www.scientific.net/KEM.800.280

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title = "Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives",

abstract = "A modular approach was used in the synthesis of the 3-(diphenylamino)carbazolyl-functionalized 2-(4-(dimethylamino)benzylidene)-1H-indene-1,3(2H)-dione (DMABI) derivatives. For this purpose, carboxyl functional group was introduced into the framework of DMABI molecule. Additionally, a regioselective method for substitution of carbonyl group of DMABI with dicyanomethylene group was investigated and verified using the heteronuclear multiple bond correlation NMR spectra. Steglich esterification method was used to connect the 3-(diphenylamino)carbazolyl moiety via an unconjugated spacer. The UV-Vis absorption spectra and molecular energy level data were obtained for the evaluation of the synthesized compounds as donor materials in bulk-heterojunction solar cells.",

keywords = "Bulk-heterojunction, Carbazole, DMABI, Organic solar cells, Regioselectivity",

author = "Armands Ruduss and Kaspars Traskovskis and Raitis Grzibovskis and Valdis Kokars",

note = "Publisher Copyright: {\textcopyright} 2019 Trans Tech Publications, Switzerland; 59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry, MSAC 2018 ; Conference date: 26-10-2018 Through 26-10-2018",

year = "2019",

doi = "10.4028/www.scientific.net/KEM.800.280",

language = "English",

isbn = "9783035714074",

series = "Key Engineering Materials",

publisher = "Trans Tech Publications Ltd",

pages = "280--285",

editor = "Maris Turks",

booktitle = "Materials Science and Applied Chemistry II",

address = "Switzerland",

}

Ruduss, A, Traskovskis, K , Grzibovskis, R & Kokars, V 2019, Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives. in M Turks (ed.), Materials Science and Applied Chemistry II. Key Engineering Materials, vol. 800 KEM, Trans Tech Publications Ltd, pp. 280-285, 59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry, MSAC 2018, Riga, Latvia, 26/10/18. https://doi.org/10.4028/www.scientific.net/KEM.800.280

Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives. / Ruduss, Armands; Traskovskis, Kaspars ; Grzibovskis, Raitis et al.
Materials Science and Applied Chemistry II. ed. / Maris Turks. Trans Tech Publications Ltd, 2019. p. 280-285 (Key Engineering Materials; Vol. 800 KEM).

Research output: Chapter in Book/Report/Conference proceeding › Conference paper › Research › peer-review

TY - GEN

T1 - Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives

AU - Ruduss, Armands

AU - Traskovskis, Kaspars

AU - Grzibovskis, Raitis

AU - Kokars, Valdis

PY - 2019

Y1 - 2019

N2 - A modular approach was used in the synthesis of the 3-(diphenylamino)carbazolyl-functionalized 2-(4-(dimethylamino)benzylidene)-1H-indene-1,3(2H)-dione (DMABI) derivatives. For this purpose, carboxyl functional group was introduced into the framework of DMABI molecule. Additionally, a regioselective method for substitution of carbonyl group of DMABI with dicyanomethylene group was investigated and verified using the heteronuclear multiple bond correlation NMR spectra. Steglich esterification method was used to connect the 3-(diphenylamino)carbazolyl moiety via an unconjugated spacer. The UV-Vis absorption spectra and molecular energy level data were obtained for the evaluation of the synthesized compounds as donor materials in bulk-heterojunction solar cells.

AB - A modular approach was used in the synthesis of the 3-(diphenylamino)carbazolyl-functionalized 2-(4-(dimethylamino)benzylidene)-1H-indene-1,3(2H)-dione (DMABI) derivatives. For this purpose, carboxyl functional group was introduced into the framework of DMABI molecule. Additionally, a regioselective method for substitution of carbonyl group of DMABI with dicyanomethylene group was investigated and verified using the heteronuclear multiple bond correlation NMR spectra. Steglich esterification method was used to connect the 3-(diphenylamino)carbazolyl moiety via an unconjugated spacer. The UV-Vis absorption spectra and molecular energy level data were obtained for the evaluation of the synthesized compounds as donor materials in bulk-heterojunction solar cells.

KW - Bulk-heterojunction

KW - Carbazole

KW - DMABI

KW - Organic solar cells

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/85071023091

U2 - 10.4028/www.scientific.net/KEM.800.280

DO - 10.4028/www.scientific.net/KEM.800.280

M3 - Conference paper

AN - SCOPUS:85071023091

SN - 9783035714074

T3 - Key Engineering Materials

SP - 280

EP - 285

BT - Materials Science and Applied Chemistry II

A2 - Turks, Maris

PB - Trans Tech Publications Ltd

T2 - 59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry, MSAC 2018

Y2 - 26 October 2018 through 26 October 2018

ER -

Synthesis and photoelectrical properties of 3-(diphenylamino)carbazolyl - Functionalized DMABI derivatives

Abstract

Publication series

Conference

UN SDGs

Keywords

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