Extending the Conjugation of Pechmann Lactone Thienyl Derivatives: A New Class of Small Molecules for Organic Electronics Application

Alessio Dessì; Matteo Bartolini; Massimo Calamante; Lorenzo Zani; Alessandro Mordini; Gianna Reginato

doi:10.1055/s-0036-1591856

Synthesis, Table of Contents

Synthesis 2018; 50(06): 1284-1292
DOI: 10.1055/s-0036-1591856

paper

Extending the Conjugation of Pechmann Lactone Thienyl Derivatives: A New Class of Small Molecules for Organic Electronics Application

Alessio Dessì

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

,

Matteo Bartolini

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

^bDipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy

,

Massimo Calamante*

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

^cDipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy

,

Lorenzo Zani

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

,

Alessandro Mordini

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

^cDipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy

,

Gianna Reginato*

^aIstituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy Email: gianna.reginato@iccom.cnr.it

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Abstract

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Abstract

The preparation and spectroscopic characterization of some symmetrical small molecules containing the disubstituted (E)-3,3′-bifuranylidene-2,2′-dione chromophore (the so-called Pechmann lactone) and featuring an extended conjugation are reported. The synthetic approach of such compounds is based on the Stille–Migita coupling reaction, which is carried out in very mild conditions, suitable to be applied with the very sensitive Pechmann core. The absorption and emission spectra of the new molecules obtained have been recorded in solution and clearly show how their photophysical properties can be modulated by a proper choice of the (hetero)aromatic terminal groups. The compounds prepared in this study (or close analogues thereof) have interesting optical properties and could find application as semiconductors in organic electronics or as near-IR fluorescent dyes.

Key words

Pechmann derivatives - organic dyes - Stille reaction - UV/Vis spectroscopy - optoelectronics

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References

References

See for instance:

1a Mazzio KA. Luscombe CK. Chem. Soc. Rev. 2015; 44: 78
1b Marinova N. Valero S. Delgado JL. J. Colloid Interface Sci. 2017; 488: 373

2a Norsten TB. Kantchev EA. B. Sullivan MB. Org. Lett. 2010; 12: 4816
2b Kantchev EA. B. Norsten TB. Tan ML. Y. Ng JJ. Y. Sullivan MB. Chem. Eur. J. 2012; 18: 695
2c Kantchev EA. B. Norsten TB. Sullivan MB. Org. Biomol. Chem. 2012; 10: 6682

3 Hayashi M. Toshimitsu F. Sakamoto R. Nishihara H. J. Am. Chem. Soc. 2011; 133: 14518

4a Efrem A. Courté M. Wang K. Fichou D. Wang M. Dyes Pigm. 2016; 134: 171
4b Cai Z. Luo H. Qi P. Wang J. Zhang G. Liu Z. Zhang D. Macromolecules 2014; 47: 2899
4c Cai Z. Liu Z. Luo H. Qi P. Zhang G. Zhang D. Chin. J. Chem. 2014; 32: 788

5 von Pechmann H. Ber. Dtsch. Chem. Ges. 1882; 15: 881
6 Kozniewski T. Marchlewski L. Anz L. Akad. Wiss. Krakau 1906; 81 ; Chem. Zentr. 1906, 2, 1189
7 Pummerer R. Buchta E. Ber. Dtsch. Chem. Ges. 1936; 69: 1018
8 Bogert MT. Ritter JJ. J. Am. Chem. Soc. 1924; 46: 2871

9a Chovin P. Bull. Chem. Soc. Fr. 1944; 11: 91
9b Klingsberg E. Chem. Rev. 1954; 54: 59

10 Fang CS. Bergmann W. J. Org. Chem. 1951; 16: 1231
11 Zhang QT. Tour JM. J. Am. Chem. Soc. 1998; 120: 5355
12 Zhang W. Moore JS. Macromolecules 2004; 37: 3973
13 Sugiyama N. Gasha T. Kataoka H. Kashima C. Bull. Chem. Soc. Jpn 1968; 41: 971
14 Hopf H. Jones PG. Nicolescu A. Bicu E. Birsa LM. Belei D. Chem. Eur. J. 2014; 20: 5565
15 Kappe CO. Stadler A. Dallinger D. Microwaves in Organic and Medicinal Chemistry . 2nd ed. Wiley-VCH; Weinheim: 2012
16 Begley MJ. Crombie L. Griffiths GL. Jones RC. F. Rahmani M. J. Chem. Soc., Chem. Commun. 1981; 823
17 Mishra A. Fischer M. Bäuerle P. Angew. Chem. Int. Ed. 2008; 48: 2474
18 Mitchell TN. Metal-catalyzed Cross-coupling Reactions . 2nd ed. Wiley-VCH; Weinheim: 2004
19 Dessì A. Calamante M. Mordini A. Zani L. Taddei M. Reginato G. RSC Adv. 2014; 3: 1322
20 Liu X. Xu Z. Cole JM. J. Phys. Chem. C 2013; 117: 16584

21a Kaeser A. Schenning AP. H. J. Adv. Mater. 2010; 22: 2985
21b Villegas C. Krokos E. Bouit P.-A. Delgado JL. Guldi DM. Martín N. Energy Environ. Sci. 2011; 4: 679
21c Bouit P.-A. Spänig F. Kuzmanich G. Krokos E. Oelsner C. Garcia-Garibay MA. Delgado JL. Martín N. Guldi DM. Chem. Eur. J. 2010; 16: 9638

22 Goncalves MS. T. Chem. Rev. 2008; 108: 190
23 Escobedo JO. Rusin O. Lim S. Strong RM. Curr. Opin. Chem. Biol. 2010; 14: 64
24 Snyder LR. J. Chromatogr. A 1974; 92: 223
25 Baheti A. Singh P. Lee C.-P. Thomas KR. J. Ho K.-C. J. Org. Chem. 2011; 76: 4910
26 Kulinich AV. Mikitenko EK. Ishchenko AA. Phys. Chem. Chem. Phys. 2016; 18: 3444
27 Quinton C. Chi S.-H. Dumas-Verdes C. Audebert P. Clavier G. Perry JW. Alain-Rizzo V. J. Mater. Chem. C 2015; 3: 8351

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