Construction of the carbon-chalcogen (S, Se, Te) bond at the
2,6-positions of BODIPY via Stille cross-coupling reaction

J 2016

Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction

PALAO UTIEL, Eduardo, Tomáš SLANINA and Petr KLÁN

Basic information

Original name

Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction

Authors

PALAO UTIEL, Eduardo (724 Spain, belonging to the institution), Tomáš SLANINA (203 Czech Republic, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Chemical communications, Cambridge, Royal Society of Chemistry, 2016, 1359-7345

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 6.319

RIV identification code

RIV/00216224:14310/16:00088610

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/c6cc06923a

UT WoS

000384203900019

Keywords in English

INTRAMOLECULAR CHARGE-TRANSFER; TRIPLET EXCITED-STATE; SINGLET OXYGEN GENERATION; LARGE STOKES SHIFTS; BORON-DIPYRROMETHENE; PHOTOPHYSICAL PROPERTIES; LIVING CELLS; DYES; DERIVATIVES; FUNCTIONALIZATION

Abstract

V originále

Seven new 2-chalcogen-or 2,6-dichalcogen-(S, Se, Te) BODIPY derivatives were synthesized in good to excellent yields (55-95%) by a Pd-catalyzed C-heteroatom Stille cross-coupling reaction, overcoming the limitations of SNAr. The fluorophores show interesting tunable optical properties associated with the formation of a twisted intramolecular charge transfer excited state and competing intersystem crossing.

Links

GA13-25775S, research and development project

Name: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

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

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

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

Citovat

PALAO UTIEL, Eduardo, Tomáš SLANINA and Petr KLÁN. Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction. Chemical communications. Cambridge: Royal Society of Chemistry, 2016, vol. 52, No 80, p. 11951-11954. ISSN 1359-7345. Available from: https://dx.doi.org/10.1039/c6cc06923a.

@article{1369916,
   author = {Palao Utiel, Eduardo and Slanina, Tomáš and Klán, Petr},
   article_location = {Cambridge},
   article_number = {80},
   doi = {http://dx.doi.org/10.1039/c6cc06923a},
   keywords = {INTRAMOLECULAR CHARGE-TRANSFER; TRIPLET EXCITED-STATE; SINGLET OXYGEN GENERATION; LARGE STOKES SHIFTS; BORON-DIPYRROMETHENE; PHOTOPHYSICAL PROPERTIES; LIVING CELLS; DYES; DERIVATIVES; FUNCTIONALIZATION},
   language = {eng},
   issn = {1359-7345},
   journal = {Chemical communications},
   title = {Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC06923A#!divAbstract},
   volume = {52},
   year = {2016}
}

TY  - JOUR
ID  - 1369916
AU  - Palao Utiel, Eduardo - Slanina, Tomáš - Klán, Petr
PY  - 2016
TI  - Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction
JF  - Chemical communications
VL  - 52
IS  - 80
SP  - 11951-11954
EP  - 11951-11954
PB  - Royal Society of Chemistry
SN  - 13597345
KW  - INTRAMOLECULAR CHARGE-TRANSFER
KW  - TRIPLET EXCITED-STATE
KW  - SINGLET OXYGEN GENERATION
KW  - LARGE STOKES SHIFTS
KW  - BORON-DIPYRROMETHENE
KW  - PHOTOPHYSICAL PROPERTIES
KW  - LIVING CELLS
KW  - DYES
KW  - DERIVATIVES
KW  - FUNCTIONALIZATION
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC06923A#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC06923A#!divAbstract
N2  - Seven new 2-chalcogen-or 2,6-dichalcogen-(S, Se, Te) BODIPY derivatives were synthesized in good to excellent yields (55-95%) by a Pd-catalyzed C-heteroatom Stille cross-coupling reaction, overcoming the limitations of SNAr. The fluorophores show interesting tunable optical properties associated with the formation of a twisted intramolecular charge transfer excited state and competing intersystem crossing.
ER  -

PALAO UTIEL, Eduardo, Tomáš SLANINA and Petr KLÁN. Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction. \textit{Chemical communications}. Cambridge: Royal Society of Chemistry, 2016, vol.~52, No~80, p.~11951-11954. ISSN~1359-7345. Available from: https://dx.doi.org/10.1039/c6cc06923a.

Detailed Information on Publication Record