Synthesis and properties of pi-conjugated donor-acceptor
macrocycles derived from phenanthrylene building blocks

J 2018

Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks

PHULWALE, Bhimrao Vaijnath; Sushil Kumar MISHRA and Ctibor MAZAL

Basic information

Original name

Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks

Authors

PHULWALE, Bhimrao Vaijnath (356 India, belonging to the institution); Sushil Kumar MISHRA (356 India, belonging to the institution) and Ctibor MAZAL (203 Czech Republic, guarantor, belonging to the institution)

Edition

Tetrahedron, Oxford, ERGAMON-ELSEVIER SCIENCE LTD, 2018, 0040-4020

Other information

Language

English

Type of outcome

Article in a journal

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Impact factor

Impact factor: 2.379

RIV identification code

RIV/00216224:14310/18:00104259

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.tet.2018.05.025

UT WoS

000436218100018

EID Scopus

2-s2.0-85047207614

Keywords in English

Macrocycles; Phenanthrene; Donor-acceptor; Solvatochromism; Intramolecular charge transfer; Sonogashira cross-coupling

Abstract

V originále

Phenanthrylene-ethynylidene macrocycles combining electron donor and electron acceptor subunits in their shape-persistent fully conjugated core were synthesized. The donor subunits consisted of two 9,10-dialkoxyphenanthrenes linked either with 1,2-ethynylidene or 2,5-thienylene bridge. The acceptors were 9,10-phenanthroquinone and dibenzoquinoxaline and dibenzophenazines derived from it. Solvatochromic photoluminescence from intramolecular-charge-transfer (ICT) excited state was observed mainly in non-polar solvents. In more polar solvents, the excited states favor non-radiative relaxation. DFT calculated HOMO/LUMO energies of the macrocycles correlate well with spectroscopic and electrochemical data. In the series of substituted dibenzophenazine acceptors a good correlation with Hammett substituent constants sigma(-)(p) was found. (C) 2018 Elsevier Ltd. All rights reserved.

Links

LQ1601, research and development project

Name: CEITEC 2020 (Acronym: CEITEC2020)

Investor: Ministry of Education, Youth and Sports of the CR

MUNI/A/1258/2016, interní kód MU

Name: Nové molekulární a nanostrukturní systémy (Acronym: NOMONA)

Investor: Masaryk University, Category A

Cite

PHULWALE, Bhimrao Vaijnath; Sushil Kumar MISHRA and Ctibor MAZAL. Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks. Tetrahedron. Oxford: ERGAMON-ELSEVIER SCIENCE LTD, 2018, vol. 74, No 27, p. 3616-3623. ISSN 0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2018.05.025.

@article{1457977,
   author = {Phulwale, Bhimrao Vaijnath and Mishra, Sushil Kumar and Mazal, Ctibor},
   article_location = {Oxford},
   article_number = {27},
   doi = {http://dx.doi.org/10.1016/j.tet.2018.05.025},
   keywords = {Macrocycles; Phenanthrene; Donor-acceptor; Solvatochromism; Intramolecular charge transfer; Sonogashira cross-coupling},
   language = {eng},
   issn = {0040-4020},
   journal = {Tetrahedron},
   title = {Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks},
   url = {https://www.sciencedirect.com/science/article/pii/S0040402018305428?via%3Dihub},
   volume = {74},
   year = {2018}
}

TY  - JOUR
ID  - 1457977
AU  - Phulwale, Bhimrao Vaijnath - Mishra, Sushil Kumar - Mazal, Ctibor
PY  - 2018
TI  - Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks
JF  - Tetrahedron
VL  - 74
IS  - 27
SP  - 3616-3623
EP  - 3616-3623
PB  - ERGAMON-ELSEVIER SCIENCE LTD
SN  - 00404020
KW  - Macrocycles
KW  - Phenanthrene
KW  - Donor-acceptor
KW  - Solvatochromism
KW  - Intramolecular charge transfer
KW  - Sonogashira cross-coupling
UR  - https://www.sciencedirect.com/science/article/pii/S0040402018305428?via%3Dihub
N2  - Phenanthrylene-ethynylidene macrocycles combining electron donor and electron acceptor subunits in their shape-persistent fully conjugated core were synthesized. The donor subunits consisted of two 9,10-dialkoxyphenanthrenes linked either with 1,2-ethynylidene or 2,5-thienylene bridge. The acceptors were 9,10-phenanthroquinone and dibenzoquinoxaline and dibenzophenazines derived from it. Solvatochromic photoluminescence from intramolecular-charge-transfer (ICT) excited state was observed mainly in non-polar solvents. In more polar solvents, the excited states favor non-radiative relaxation. DFT calculated HOMO/LUMO energies of the macrocycles correlate well with spectroscopic and electrochemical data. In the series of substituted dibenzophenazine acceptors a good correlation with Hammett substituent constants sigma(-)(p) was found. (C) 2018 Elsevier Ltd. All rights reserved.
ER  -

PHULWALE, Bhimrao Vaijnath; Sushil Kumar MISHRA and Ctibor MAZAL. Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks. \textit{Tetrahedron}. Oxford: ERGAMON-ELSEVIER SCIENCE LTD, 2018, vol.~74, No~27, p.~3616-3623. ISSN~0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2018.05.025.

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