Synlett 2024; 35(14): 1629-1647
DOI: 10.1055/a-2191-6011
account

Polyconjugated Materials for Printed (Opto)Electronics: Introducing Sustainability

Mauro Sassi
,
Sara Mattiello
,
Alice Fappani
,
Luca Beverina
This work was supported by the Italian Ministry of University and Research (MIUR; Grant Dipartimenti di Eccellenza-2017 ‘Materials for Energy’) through the grant PRIN2017 BOOSTER (project no. 2017YXX8AZ).


This work is dedicated to the memory of Prof. Giorgio A. Pagani.

Abstract

This account summarizes the impact that the quest for sustainability is having on the field of organic polyconjugate molecules and polymers for plastic (opto)electronics. While at the proof-of-concept level, the design criteria as well as the preferred synthetic strategies to access new and improved materials have been dominated by the need for performance. The ongoing transition from the lab environment to the industrial scale imposes strict limitations on the cost and overall environmental impact of new materials. We here summarize our efforts on the development of new design criteria and synthetic strategies aimed at improving sustainability – without compromising performance – in organic polyconjugated molecules. The article is composed of three sections: Introduction and motivation, sustainability through improved synthetic methods and through improved design.

Outline

1 Introduction and Motivation

2 Sustainable Reaction Methods

2.1 The New Tools: Reactions in Aqueous Solution of Surfactants

2.2 Intrinsically More Sustainable Reactions: Direct Arylation

2.3 Sustainable Multistep Protocols: Combining Micellar, Solventless, and Mechanochemical Methods

3 Sustainability as a Design Criterion: De Novo Design

4 Conclusion



Publication History

Received: 21 September 2023

Accepted after revision: 13 October 2023

Accepted Manuscript online:
13 October 2023

Article published online:
20 November 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Paterson AF, Singh S, Fallon KJ, Hodsden T, Han Y, Schroeder BC, Bronstein H, Heeney M, McCulloch I, Anthopoulos TD. Adv. Mater. 2018; 30: 1801079
  • 2 Pan M.-A, Lau T.-K, Tang Y, Wu Y.-C, Liu T, Li K, Chen M.-C, Lu X, Ma W, Zhan C. J. Mater. Chem. A 2019; 7: 20713
  • 3 Zhang Z.-G, Li Y. Angew. Chem. Int. Ed. 2021; 60: 4422
  • 4 Griggs S, Marks A, Bristow H, McCulloch I. J. Mater. Chem. C 2021; 9: 8099
  • 5 Wen T.-J, Liu Z.-X, Chen Z, Zhou J, Shen Z, Xiao Y, Lu X, Xie Z, Zhu H, Li C.-Z, Chen H. Angew. Chem. Int. Ed. 2021; 60: 12964
  • 6 Markina A, Lin K.-H, Liu W, Poelking C, Firdaus Y, Villalva DR, Khan JI, Paleti SH. K, Harrison GT, Gorenflot J, Zhang W, De Wolf S, McCulloch I, Anthopoulos TD, Baran D, Laquai F, Andrienko D. Adv. Energy Mater. 2021; 11: 2170175
  • 7 Cui Y, Yao H, Zhang J, Xian K, Zhang T, Hong L, Wang Y, Xu Y, Ma K, An C, He C, Wei Z, Gao F, Hou J. Adv. Mater. 2020; 32: 1908205
  • 8 Guo H, Yang C.-Y, Zhang X, Motta A, Feng K, Xia Y, Shi Y, Wu Z, Yang K, Chen J, Liao Q, Tang Y, Sun H, Woo HY, Fabiano S, Facchetti A, Guo X. Nature 2021; 599: 67
  • 9 Wang C, Yokota T, Someya T. Chem. Rev. 2021; 121: 2109
  • 10 Wu J, Li Z, Luo J, Jen AK.-Y. J. Mater. Chem. C 2020; 8: 15009
  • 11 Dalton LR, Sullivan PA, Bale DH. Chem. Rev. 2010; 110: 25
  • 12 Huang Y, Elder DL, Kwiram AL, Jenekhe SA, Jen AK. Y, Dalton LR, Luscombe CK. Adv. Mater. 2021; 33: 1904239
  • 13 Li T, Wu Y, Zhou J, Li M, Wu J, Hu Q, Jia B, Pan X, Zhang M, Tang Z, Xie Z, Russell TP, Zhan X. J. Am. Chem. Soc. 2020; 142: 20124
  • 14 Xue P, Calascibetta AM, Chen K, Thorn KE, Jiang Y, Shi J, Jia B, Li M, Xin J, Cai G, Yang R, Lu H, Mattiello S, Liu Y, Tang Z, Ma W, Lu X, Meng Q, Hodgkiss JM, Beverina L, Han RP. S, Zhan X. J. Mater. Chem. A 2022; 10: 24073
  • 15 Tsai K, Hung M, Mao Y, Chen S. Adv. Funct. Mater. 2019; 29: 1901025
  • 16 Liu Y, Li C, Ren Z, Yan S, Bryce MR. Nat. Rev. Mater. 2018; 3: 18020
  • 17 Zhang W, Wen J, Yang J, Li M, Peng F, Ma M, Bian J. Int. J. Biol. Macromol. 2022; 223: 1
  • 18 Kim JH, Kim S.-M, Kim G, Yoon M.-H. Macromol. Biosci. 2020; 20: 2000211
  • 19 Evans AM, Bradshaw NP, Litchfield B, Strauss MJ, Seckman B, Ryder MR, Castano I, Gilmore C, Gianneschi NC, Mulzer CR, Hersam MC, Dichtel WR. Adv. Mater. 2020; 32: 2004205
  • 20 Jia Y, Shen L, Liu J, Zhou W, Du Y, Xu J, Liu C, Zhang G, Zhang Z, Jiang F. J. Mater. Chem. C 2019; 7: 3496
  • 21 Chen Y, Wang C. Acc. Chem. Res. 2020; 53: 2636
  • 22 Koenig JD. B, Hoff A, Gasonoo A, Welch GC. Chem. Mater. 2023; 35: 251
  • 23 Gerasimov JY, Halder A, Mousa AH, Ghosh S, Harikesh PC, Abrahamsson T, Bliman D, Strandberg J, Massetti M, Zozoulenko I, Simon DT, Berggren M, Olsson R, Fabiano S. Adv. Funct. Mater. 2022; 32: 2202292
  • 24 Fresta E, Costa R. e nD. J. Mater. Chem. C 2017; 5: 5643
  • 25 Marks A, Chen X, Wu R, Rashid RB, Jin W, Paulsen BD, Moser M, Ji X, Griggs S, Meli D, Wu X, Bristow H, Strzalka J, Gasparini N, Costantini G, Fabiano S, Rivnay J, McCulloch I. J. Am. Chem. Soc. 2022; 144: 4642
  • 26 Zhao W, Ding J, Zou Y, Di C, Zhu D. Chem. Soc. Rev. 2020; 49: 7210
  • 27 Macher S, Schott M, Sassi M, Facchinetti I, Ruffo R, Patriarca G, Beverina L, Posset U, Giffin GA, Löbmann P. Adv. Funct. Mater. 2020; 30: 1906254
  • 28 Pang S, Gao Y, Choi S. Adv. Energy Mater. 2018; 8: 1702261
  • 29 Yiğit D, Güllü M. J. Mater. Chem. A 2017; 5: 609
  • 30 Wang L, Chen D, Jiang K, Shen G. Chem. Soc. Rev. 2017; 46: 6764
  • 31 Sharova AS, Melloni F, Lanzani G, Bettinger CJ, Caironi M. Adv. Mater. Technol. 2021; 6: 2000757
  • 32 Bonacchini GE, Bossio C, Greco F, Mattoli V, Kim Y.-H, Lanzani G, Caironi M. Adv. Mater. 2018; 30: 1706091
  • 33 Tang H, Lin P, Chan HL. W, Yan F. Biosens. Bioelectron. 2011; 26: 4559
  • 34 Zhang X, Zhang X, Sun L, Liu F, Wang M, Peng J, Wang Y, Ma L, Wang B, Wei H. Chem. Commun. 2018; 54: 13495
  • 35 Mun J, Wang G.-JN, Oh JY, Katsumata T, Lee FL, Kang J, Wu H.-C, Lissel F, Rondeau-Gagné S, Tok JB.-H, Bao Z. Adv. Funct. Mater. 2018; 28: 1804222
  • 36 Feig VR, Tran H, Bao Z. ACS Cent. Sci. 2018; 4: 337
  • 37 Galagan Y. Oxford Open Mater. Sci. 2021; 1, itaa007
  • 38 Po R, Bernardi A, Calabrese A, Carbonera C, Corso G, Pellegrino A. Energy Environ. Sci. 2014; 7: 925
  • 39 Po R, Bianchi G, Carbonera C, Pellegrino A. Macromolecules 2015; 48: 453
  • 40 Liao C.-Y, Hsiao Y.-T, Tsai K.-W, Teng N.-W, Li W.-L, Wu J.-L, Kao J.-C, Lee C.-C, Yang C.-M, Tan H.-S, Chung K.-H, Chang Y.-M. Sol. RRL 2021; 5: 2000749
  • 41 Facchetti A, Annoni E, Beverina L, Morone M, Zhu P, Marks TJ, Pagani GA. Nat. Mater. 2004; 3: 910
  • 42 Beverina L, Fu J, Leclercq A, Zojer E, Pacher P, Barlow S, Van Stryland EW, Hagan DJ, Brédas J.-L, Marder SR. J. Am. Chem. Soc. 2005; 127: 7282
  • 43 Chung S.-J, Zheng S, Odani T, Beverina L, Fu J, Padilha LA, Biesso A, Hales JM, Zhan X, Schmidt K, Ye A, Zojer E, Barlow S, Hagan DJ, Van Stryland EW, Yi Y, Shuai Z, Pagani GA, Brédas J.-L, Perry JW, Marder SR. J. Am. Chem. Soc. 2006; 128: 14444
  • 44 Abbotto A, Beverina L, Manfredi N, Pagani GA, Archetti G, Kuball H.-G, Wittenburg C, Heck J, Holtmann J. Chem. Eur. J. 2009; 15: 6175
  • 45 Beverina L, Abbotto A, Landenna M, Cerminara M, Tubino R, Meinardi F, Bradamante S, Pagani GA. Org. Lett. 2005; 7: 4257
  • 46 Morone M, Beverina L, Abbotto A, Silvestri F, Collini E, Ferrante C, Bozio R, Pagani GA. Org. Lett. 2006; 8: 2719
  • 47 Beverina L, Crippa M, Landenna M, Ruffo R, Salice P, Silvestri F, Versari S, Villa A, Ciaffoni L, Collini E, Ferrante C, Bradamante S, Mari CM, Bozio R, Pagani GA. J. Am. Chem. Soc. 2008; 130: 1894
  • 48 Rapozzi V, Beverina L, Salice P, Pagani GA, Camerin M, Xodo LE. J. Med. Chem. 2010; 53: 2188
  • 49 Silvestri F, Irwin MD, Beverina L, Facchetti A, Pagani GA, Marks TJ. J. Am. Chem. Soc. 2008; 130: 17640
  • 50 Beverina L, Ruffo R, Mari CM, Pagani GA, Sassi M, De Angelis F, Fantacci S, Yum J.-H, Grätzel M, Nazeeruddin MK. ChemSusChem 2009; 2: 621
  • 51 Binda M, Agostinelli T, Caironi M, Natali D, Sampietro M, Beverina L, Ruffo R, Silvestri F. Org. Electron. 2009; 10: 1314
  • 52 Bagnis D, Beverina L, Huang H, Silvestri F, Yao Y, Yan H, Pagani GA, Marks TJ, Facchetti A. J. Am. Chem. Soc. 2010; 132: 4074
  • 53 Beverina L, Ruffo R, Salamone MM, Ronchi E, Binda M, Natali D, Sampietro M. J. Mater. Chem. 2012; 22: 6704
  • 54 Beverina L, Salice P. Eur. J. Org. Chem. 2010; 1207
  • 55 Beverina L, Sassi M. Synlett 2014; 25: 477
  • 56 Schimperna G, Beverina L, Sassi M. WO 2019138332 A1 2019
  • 57 Ligault B, Lapointe D, Caron L, Vlassova A, Fagnou K. J. Org. Chem. 2009; 74: 1826
  • 58 Facchetti A, Vaccaro L, Marrocchi A. Angew. Chem. Int. Ed. 2012; 51: 3520
  • 59 Lipshutz BH. Synlett 2021; 32: 1588
  • 60 Cortes-Clerget M, Yu J, Kincaid JR. A, Walde P, Gallou F, Lipshutz BH. Chem. Sci. 2021; 12: 4237
  • 61 Cortes-Clerget M, Akporji N, Zhou J, Gao F, Guo P, Parmentier M, Gallou F, Berthon J.-Y, Lipshutz BH. Nat. Commun. 2019; 10: 2169
  • 62 Lipshutz BH, Ghorai S, Cortes-Clerget M. Chem. Eur. J. 2018; 24: 6672
  • 63 Handa S, Wang Y, Gallou F, Lipshutz BH. Science 2015; 349: 1087
  • 64 Lipshutz BH, Ghorai S. Aldrichimica Acta 2012; 45: 3
  • 65 Rahmanudin A, Marcial-Hernandez R, Zamhuri A, Walton AS, Tate DJ, Khan RU, Aphichatpanichakul S, Foster AB, Broll S, Turner ML. Adv. Sci. 2020; 7: 2002010
  • 66 Ceriani C, Scagliotti M, Losi T, Luzio A, Mattiello S, Sassi M, Pianta N, Rapisarda M, Mariucci L, Caironi M, Beverina L. Adv. Electron. Mater. 2023; 2201160
  • 67 Ceriani C, Corsini F, Mattioli G, Mattiello S, Testa D, Po R, Botta C, Griffini G, Beverina L. J. Mater. Chem. C 2021; 9: 14815
  • 68 Mattiello S, Sanzone A, Bruni F, Gandini M, Pinchetti V, Monguzzi A, Facchinetti I, Ruffo R, Meinardi F, Mattioli G, Sassi M, Brovelli S, Beverina L. Joule 2020; 4: 1988
  • 69 Wakioka M, Ozawa F. Asian J. Org. Chem. 2018; 7; 1206
  • 70 Nitti A, Bianchi G, Po R, Swager TM, Pasini D. J. Am. Chem. Soc. 2017; 139: 8788
  • 71 Pouliot J.-R, Grenier F, Blaskovits JT, Beaupré S, Leclerc M. Chem. Rev. 2016; 116: 14225
  • 72 Marzano G, Carulli F, Babudri F, Pellegrino A, Po R, Luzzati S, Farinola GM. J. Mater. Chem. A 2016; 4: 17163
  • 73 Dudnik AS, Aldrich TJ, Eastham ND, Chang RP. H, Facchetti A, Marks TJ. J. Am. Chem. Soc. 2016; 138: 15699
  • 74 Rudenko AE, Thompson BC. J. Polym. Sci., Part A: Polym. Chem. 2015; 53: 135
  • 75 Morin P.-O, Bura T, Sun B, Gorelsky SI, Li Y, Leclerc M. ACS Macro Lett. 2015; 4: 21
  • 76 Matsidik R, Komber H, Luzio A, Caironi M, Sommer M. J. Am. Chem. Soc. 2015; 137: 6705
  • 77 Facchetti A, Vaccaro L, Marrocchi A. Angew. Chem. Int. Ed. 2012; 51: 3520
  • 78 Moser M, Wadsworth A, Gasparini N, McCulloch I. Adv. Energy Mater. 2021; 11: 2100056
  • 79 Al-Ahmad AY, Almayhi F, Al-Mudhaffer MF, Griffith MJ, Liu W, Li S, Sivunova K, Elkington D, Cooling NA, Feron K, Shi M, Belcher W, Chen H, Dastoor P, Andersen TR. Sustainable Energy Fuels 2020; 4: 940
  • 80 Sassi M, Mattiello S, Beverina L. Eur. J. Org. Chem. 2020; 3942
  • 81 Mattiello S, Ghiglietti E, Zucchi A, Beverina L. Curr. Opin. Colloid Interface Sci. 2023; 101681
  • 82 Lorenzetto T, Frigatti D, Fabris F, Scarso A. Adv. Synth. Catal. 2022; 364: 1776
  • 83 La Sorella G, Strukul G, Scarso A. Green Chem. 2015; 17: 644
  • 84 Lipshutz BH, Ghorai S. Green Chem. 2014; 16: 3660
  • 85 Lipshutz BH, Ghorai S, Abela AR, Moser R, Nishikata T, Duplais C, Krasovskiy A, Gaston RD, Gadwood RC. J. Org. Chem. 2011; 76: 4379
  • 86 Lipshutz BH, Abela AR. Org. Lett. 2008; 10: 5329
  • 87 Gröger H, Gallou F, Lipshutz BH. Chem. Rev. 2023; 123 (09) 5262 ; DOI: DOI: 10.1021/acs.chemrev.2c00416.
  • 88 Klumphu P, Lipshutz BH. J. Org. Chem. 2014; 79: 888
  • 89 Ceriani C, Ghiglietti E, Sassi M, Mattiello S, Beverina L. Org. Process Res. Dev. 2020; 24: 2604
  • 90 Mattiello S, Monguzzi A, Pedrini J, Sassi M, Villa C, Torrente Y, Marotta R, Meinardi F, Beverina L. Adv. Funct. Mater. 2016; 26: 8447
  • 91 Petros RA, DeSimone JM. Nat. Rev. Drug Discovery 2010; 9: 615
  • 92 Mattiello S, Rooney M, Sanzone A, Brazzo P, Sassi M, Beverina L. Org. Lett. 2017; 19: 654
  • 93 Thakore RR, Takale BS, Hu Y, Ramer S, Kostal J, Gallou F, Lipshutz BH. Tetrahedron 2021; 87: 132090
  • 94 Lee NR, Cortes-Clerget M, Wood AB, Lippincott DJ, Pang H, Moghadam FA, Gallou F, Lipshutz BH. ChemSusChem 2019; 12: 3159
  • 95 Cortes-Clerget M, Spink SE, Gallagher GP, Chaisemartin L, Filaire E, Berthon J.-Y, Lipshutz BH. Green Chem. 2019; 21: 2610
  • 96 Klumphu P, Lipshutz BH. J. Org. Chem. 2014; 79: 888
  • 97 Sharma S, Ansari TN, Handa S. ACS Sustainable Chem. Eng. 2021; 9: 12719
  • 98 Handa S, Ibrahim F, Ansari TN, Gallou F. ChemCatChem 2018; 10: 4229
  • 99 Bianchi G, Po R, Sassi M, Beverina L, Chiaberge S, Spera S, Cominetti A. ACS OMEGA 2017; 2: 4347
  • 100 Gabriel CM, Lee NR, Bigorne F, Klumphu P, Parmentier M, Gallou F, Lipshutz BH. Org. Lett. 2017; 19: 194
  • 101 Hauk P, Wencel-Delord J, Ackermann L, Walde P, Gallou F. Curr. Opin. Colloid Interface Sci. 2021; 56: 101506
  • 102 Lippincott DJ, Landstrom E, Cortes-Clerget M, Lipshutz BH, Buescher K, Schreiber R, Durano C, Parmentier M, Ye N, Wu B, Shi M, Yang H, Andersson M, Gallou F. Org. Process Res. Dev. 2020; 24: 841
  • 103 Serrano-Luginbühl S, Ruiz-Mirazo K, Ostaszewski R, Gallou F, Walde P. Nat. Rev. Chem. 2018; 2: 306
  • 104 Rooney M, Mattiello S, Stara R, Sanzone A, Brazzo P, Sassi M, Beverina L. Dyes Pigm. 2018; 149: 893
  • 105 Maqueira-Albo I, Bonacchini GE, Dell’Erba G, Pace G, Sassi M, Rooney M, Resel R, Beverina L, Caironi M. J. Mater. Chem. C 2017; 5: 11522
  • 106 Beverina L, Rooney M, Ruffo R, Sassi M, Carulli F, Luzzati S, Resel R, Schrode B. Org. Photonics Photovolt. 2018; 6: 8
  • 107 Mattiello S, Sanzone A, Brazzo P, Sassi M, Beverina L. Eur. J. Org. Chem. 2015; 5723
  • 108 Sanzone A, Calascibetta A, Monti M, Mattiello S, Sassi M, Corsini F, Griffini G, Sommer M, Beverina L. ACS Macro Lett. 2020; 9: 1167
  • 109 Behrendt JM, Esquivel Guzman JA, Purdie L, Willcock H, Morrison JJ, Foster AB, O’Reilly RK, McCairn MC, Turner ML. React. Funct. Polym. 2016; 107: 69
  • 110 Muenmart D, Foster AB, Harvey A, Chen M.-T, Navarro O, Promarak V, McCairn MC, Behrendt JM, Turner ML. Macromolecules 2014; 47: 6531
  • 111 Brocklehurst CE, Gallou F, Hartwieg JC. D, Palmieri M, Rufle D. Org. Process Res. Dev. 2018; 22: 1453
  • 112 Riehm DA, Rokke DJ, Paul PG, Lee HS, Vizanko BS, McCormick AV. J. Colloid Interface Sci. 2017; 487: 52
  • 113 Ceriani C, Pallini F, Mezzomo L, Sassi M, Mattiello S, Beverina L. J. Organomet. Chem. 2022; 962: 122267
  • 114 Wang B, Tsang S.-W, Zhang W, Tao Y, Wong MS. Chem. Commun. 2011; 47: 9471
  • 115 Gu Z, Shen P, Tsang S.-W, Tao Y, Zhao B, Tang P, Nie Y, Fang Y, Tan S. Chem. Commun. 2011; 47: 9381
  • 116 Zeng S, Yin L, Ji C, Jiang X, Li K, Li Y, Wang Y. Chem. Commun. 2012; 48: 10627
  • 117 Beaujuge PM, Tsao HN, Hansen MR, Amb CM, Risko C, Subbiah J, Choudhury KR, Mavrinskiy A, Pisula W, Brédas J.-L, So F, Müllen K, Reynolds JR. J. Am. Chem. Soc. 2012; 134: 8944
  • 118 He C.-Y, Wu C.-Z, Qing F.-L, Zhang X. J. Org. Chem. 2014; 79: 1712
  • 119 Sanzone A, Calascibetta A, Ghiglietti E, Ceriani C, Mattioli G, Mattiello S, Sassi M, Beverina L. J. Org. Chem. 2018; 83: 15029
  • 120 Sanzone A, Mattiello S, Garavaglia GM, Calascibetta AM, Ceriani C, Sassi M, Beverina L. Green Chem. 2019; 21: 4400
  • 121 Takimiya K, Ebata H, Sakamoto K, Izawa T, Otsubo T, Kunugi Y. J. Am. Chem. Soc. 2006; 128: 12604
  • 122 Ebata H, Izawa T, Miyazaki E, Takimiya K, Ikeda M, Kuwabara H, Yui T. J. Am. Chem. Soc. 2007; 129: 15732
  • 123 Um M.-C, Kwak J, Hong J.-P, Kang J, Yoon DY, Lee SH, Lee C, Hong J.-I. J. Mater. Chem. 2008; 18: 4698
  • 124 Saito M, Osaka I, Miyazaki E, Takimiya K, Kuwabara H, Ikeda M. Tetrahedron Lett. 2011; 52: 285
  • 125 Ruzié C, Karpinska J, Kennedy AR, Geerts YH. J. Org. Chem. 2013; 78: 7741
  • 126 Schweicher G, Lemaur V, Niebel C, Ruzié C, Diao Y, Goto O, Lee W.-Y, Kim Y, Arlin J.-B, Karpinska J, Kennedy AR, Parkin SR, Olivier Y, Mannsfeld SC. B, Cornil J, Geerts YH, Bao Z. Adv. Mater. 2015; 20: 3066
  • 127 Brals J, Smith JD, Ibrahim F, Gallou F, Handa S. ACS Catal. 2017; 7: 7245
  • 128 Finck L, Brals J, Pavuluri B, Gallou F, Handa S. J. Org. Chem. 2018; 83: 7366
  • 129 Smith JD, Ansari TN, Andersson MP, Yadagiri D, Ibrahim F, Liang S, Hammond GB, Gallou F, Handa S. Green Chem. 2018; 20: 1784
  • 130 Kato K, Kimura S, Kusamoto T, Nishihara H, Teki Y. Angew. Chem. Int. Ed. 2019; 58: 2606
  • 131 Hattori Y, Kusamoto T, Nishihara H. Angew. Chem. Int. Ed. 2014; 53: 11845
  • 132 Hattori Y, Kitajima R, Ota W, Matsuoka R, Kusamoto T, Sato T, Uchida K. Chem. Sci. 2022; 13: 13418
  • 133 Mattiello S, Corsini F, Mecca S, Sassi M, Ruffo R, Mattioli G, Hattori Y, Kusamoto T, Griffini G, Beverina L. Mater. Adv. 2021; 2: 7369
  • 134 Mattiello S, Hattori Y, Kitajima R, Matsuoka R, Kusamoto T, Uchida K, Beverina L. J. Mater. Chem. C 2022; 10: 15028
  • 135 Mattiello S, Mecca S, Ronchi A, Calascibetta A, Mattioli G, Pallini F, Meinardi F, Beverina L, Monguzzi A. ACS Energy Lett. 2022; 2435
  • 136 Sangachin MH, Brassard S, Leclerc M. J. Org. Chem. 2023; 88: 3303
  • 137 Yadav P, Velmurugan N, Luscombe CK. Synthesis 2023; 55: 1
  • 138 Matsidik R, Komber H, Brinkmann M, Schellhammer KS, Ortmann F, Sommer M. J. Am. Chem. Soc. 2023; 145: 8430
  • 139 Chakraborty B, Luscombe CK. Angew. Chem. Int. Ed. 2023; 62: e202301247
  • 140 Brassard S, Sangachin MH, Leclerc M. Macromolecules 2023; 56: 1362
  • 141 Mayhugh AL, Yadav P, Luscombe CK. J. Am. Chem. Soc. 2022; 144: 6123
  • 142 Wang Q, Lenjani SV, Dolynchuk O, Scaccabarozzi AD, Komber H, Guo Y, Guenther F, Gemming S, Magerle R, Caironi M, Sommer M. Chem. Mater. 2021; 33: 668
  • 143 Anthony JE, Facchetti A, Heeney M, Marder SR, Zhan X. Adv. Mater. 2010; 22: 3876
  • 144 Liu J, Qiu L, Alessandri R, Qiu X, Portale G, Dong J, Talsma W, Ye G, Sengrian AA, Souza PC. T, Loi MA, Chiechi RC, Marrink SJ, Hummelen JC, Koster LJ. A. Adv. Mater. 2018; 30: 1704630
  • 145 Werner A, Li F, Harada K, Pfeiffer M, Fritz T, Leo K, Machill S. Adv. Funct. Mater. 2004; 14: 255
  • 146 Kolesov VA, Fuentes-Hernandez C, Chou W.-F, Aizawa N, Larrain FA, Wang M, Perrotta A, Choi S, Graham S, Bazan GC, Nguyen T.-Q, Marder SR, Kippelen B. Nat. Mater. 2017; 16: 474
  • 147 Yan H, Chen Z, Zheng Y, Newman C, Quinn JR, Dötz F, Kastler M, Facchetti A. Nature 2009; 457: 679
  • 148 Viola FA, Melloni F, Molazemhosseini A, Modena F, Sassi M, Beverina L, Caironi M. Adv. Electron. Mater. 2023; 9: 2200573
  • 149 Giovannitti A, Nielsen CB, Sbircea D.-T, Inal S, Donahue M, Niazi MR, Hanifi DA, Amassian A, Malliaras GG, Rivnay J, McCulloch I. Nat. Commun. 2016; 7: 13066
  • 150 Calascibetta AM, Mattiello S, Sanzone A, Facchinetti I, Sassi M, Beverina L. Molecules 2020; 25: 3717
  • 151 Mainville M, Tremblay V, Fenniri MZ, Laventure A, Farahat ME, Ambrose R, Welch GC, Hill IG, Leclerc M. Asian J. Org. Chem. 2020; 9: 1318
  • 152 Discekici EH, Treat NJ, Poelma SO, Mattson KM, Hudson ZM, Luo Y, Hawker CJ, de Alaniz JR. Chem. Commun. 2015; 51: 11705
  • 153 Eisenreich F, Meijer EW, Palmans AR. A. Chem. Eur. J. 2020; 26: 10355
  • 154 Poelma SO, Burnett GL, Discekici EH, Mattson KM, Treat NJ, Luo Y, Hudson ZM, Shankel SL, Clark PG, Kramer JW, Hawker CJ, Read de Alaniz J. J. Org. Chem. 2016; 81: 7155
  • 155 Chatterjee T, Iqbal N, You Y, Cho EJ. Acc. Chem. Res. 2016; 49: 2284
  • 156 Majek M, Jacobi von Wangelin A. Acc. Chem. Res. 2016; 49: 2316
  • 157 Marchini M, Bergamini G, Cozzi PG, Ceroni P, Balzani V. Angew. Chem. Int. Ed. 2017; 56: 12820
  • 158 Bu M, Cai C, Gallou F, Lipshutz BH. Green Chem. 2018; 20: 1233
  • 159 Santos MS, Cybularczyk-Cecotka M, König B, Giedyk M. Chem. Eur. J. 2020; 26: 15323
  • 160 Arora A, Weaver JD. Org. Lett. 2016; 18: 3996
  • 161 Pallini F, Sangalli E, Sassi M, Roth PM. C, Mattiello S, Beverina L. Org. Biomol. Chem. 2021; 19: 3016
  • 162 Ranaudo A, Greco C, Moro G, Zucchi A, Mattiello S, Beverina L, Cosentino U. J. Phys. Chem. B 2022; 126: 9408
  • 163 Mattiello S, Lucarelli G, Calascibetta AM, Polastri L, Ghiglietti E, Kumar Podapangi S, Brown TM, Sassi M, Beverina L. ACS Sustainable Chem. Eng. 2022; 10: 4750
  • 164 Leijtens T, Giovenzana T, Habisreutinger SN, Tinkham JS, Noel NK, Kamino BA, Sadoughi G, Sellinger A, Snaith HJ. ACS Appl. Mater. Interfaces 2016; 8: 5981
  • 165 Wu R, Schumm JS, Pearson DL, Tour JM. J. Org. Chem. 1996; 61: 6906
  • 166 Poriel C, Ferrand Y, Juillard S, Le Maux P, Simonneaux G. Tetrahedron 2004; 60: 145
  • 167 Jeon NJ, Lee HG, Kim YC, Seo J, Noh JH, Lee J, Seok SI. J. Am. Chem. Soc. 2014; 136: 7837
  • 168 Bhanuchandra M, Yorimitsu H, Osuka A. Org. Lett. 2016; 18: 384
  • 169 Ghiglietti E, Podapangi S, Mecca S, Mezzomo L, Ruffo R, Sassi M, Mattiello S, Brown TM, Beverina L. Energy Adv. 2022; 1: 398
  • 170 Vaghi L, Sanzone A, Sassi M, Pagani S, Papagni A, Beverina L. Synthesis 2018; 50: 1621
  • 171 Liu K, Brivio M, Xiao T, Norwood VM. I, Kim YS, Jin S, Papagni A, Vaghi L, Huigens RW. I. ACS Infect. Dis. 2022; 8: 280
  • 172 Delgado-Sanchez J.-M. Sol. Energy Mater. Sol. Cells 2019; 202: 110134
  • 173 Griffini G. Front. Mater. 2019; 6: 3453
  • 174 Wang Y, Michinobu T. J. Mater. Chem. C 2016; 4: 6200
  • 175 Zhang J, Chen W, Rojas AJ, Jucov EV, Timofeeva TV, Parker TC, Barlow S, Marder SR. J. Am. Chem. Soc. 2013; 135: 16376