RESEARCH ARTICLE
www.m c-jou nal.de
The Role o Polyme –AuNP In e ac ion in he
S imuli-Response P ope ies o PPA–AuNP Nanocomposi es
Manuel Núñez-Ma ínez, Sand a A ias, Julián Be guei o, Emilio Quiñoá, Rica do Rigue a,
and Félix F ei e*
The helical sense con ol o dynamic helical polyme s such as
poly(phenylace ylene)s (PPAs) is g ea ly affec ed when hey a e conjuga ed o
AuNPs h ough a s ong hiol-Au connec ion, which es ic s con o ma ional
changes a he polyme . Thus, he classical hiol-MNP bonds mus be
eplaced by weake ones, such as sup amolecula amide–Au in e ac ions. A
s aigh o wa d p epa a ion o he PPA–Au nanocomposi e by educ ion o a
p e o med PPA–Au3+complex canno be used due o a edox eac ion
be ween he wo componen s o he complex which deg ades he polyme . To
a oid he in e ac ion be ween he PPA and he Au3+ions be o e he educ ion
akes place, he me al ions a e added o he polyme solu ion capped as a
TOAB complex, which keeps he PPA s able due o he lack o PPA–Au3+
in e ac ions. Ul e io educ ion o he Au3+ions by NaBH4affo ds he desi ed
nanocomposi e, whe e he AuNPs a e s abilized by sup amolecula
anilide–AuNPs in e ac ions. By using his app oach, 3.7 nm gold
nanopa icles a e gene a ed and aligned along he polyme chain wi h a
egula dis ance be ween pa icles o 6 nm ha co esponds o wo helical
pi ches. These nanocomposi es show s imuli- esponsi e p ope ies and a e
also able o o m mac oscopically chi al nanosphe es wi h unable size.
1. In oduc ion
Me al nanopa icles (MNPs) ha e been deeply s udied du ing he
las decades due o hei applica ions in fields such as sensing,[1]
biomedicine,[2,3] and ca alysis,[4] among o he s. MNPs can be
p epa ed using diffe en p o ocols ha usually affec hei size
and shape.[5,6] Mo eo e , depending on he s uc u al cha ac-
e is ics o he o ganic molecules used as p o ec ing agen s
o coa ings—small molecules/polyme s, cha ged/neu al, hy-
d ophobic/hyd ophilic, e c.—o he p ope ies in addi ion o he
M. Núñez-Ma ínez, S. A ias, J. Be guei o, E. Quiñoá, R. Rigue a, F. F ei e
Cen o Singula de In es igación en Química Biolóxica e Ma e iais
Molecula es (CiQUS) and Depa amen o de Química O gánica
Uni e sidade de San iago de Compos ela
E-15782 San iago de Compos ela, Spain
E-mail: [email p o ec ed]
© 2021 The Au ho s. Mac omolecula Rapid Communica ions published
by Wiley-VCH GmbH. This is an open access a icle unde he e ms o
he C ea i e Commons A ibu ion-NonComme cial-NoDe i s License,
which pe mi s use and dis ibu ion in any medium, p o ided he o iginal
wo k is p ope ly ci ed, he use is non-comme cial and no modifica ions
o adap a ions a e made.
DOI: 10.1002/ma c.202100616
size o shape o he pa icles may also
be affec ed, such as s abili y, solubili y, o
biocompa ibili y. In he li e a u e, he e a e
se e al examples o nanocomposi es ha
combine helical mac omolecules wi h ele-
an biological unc ions (p o eins o DNA)
wi h MNPs.[7–9] In hose cases, he helical
sense o he biomac omolecule in he
composi e is fixed and de e mined by he
chi ali y o he esidues used o build he
mac omolecule. Howe e , he p epa a ion
o mo e appealing nanocomposi es made
o dynamic helical polyme s[10–38]—such
as poly(phenylace ylene)s (PPAs)—and
MNPs, has been sca cely explo ed.[39–41]
These polyme s can une hei helical
s uc u e—sense and/o elonga ion—
using diffe en ex e nal s imuli such as
me al ions, sol en pola i y, o empe a-
u e, and he e o e can p o ide in e es ing
p ope ies o he nanocomposi es. How-
e e , depending on he p o ocol used o
p epa e he nanocomposi e, he dynamic
beha io o he polyme can be la gely
affec ed. Thus, he dynamic beha io s o PPAs such as poly-
(R)-1 ha bea s he 4-anilide o (R)-𝛼-me hoxy-𝛼-phenylace ic
acid as pendan g oup, o poly-(R)-2, ha bea s he 4-benzamide
o (S)-phenylglycine me hyl es e as pendan a e d ama ically
educed when he polyme s a e a ached o a me al nanopa -
icles h ough he use o hiol-me al bonds—i.e., poly-[(R)-
1-co- hiol-MNP] nanocomposi e (M =Au o Ag)— o o m
he nanocomposi es.[39] This p oblem was su passed by us-
ing sup amolecula chemis y o link he PPA o he me al
nanopa icle ins ead o a mo e “co alen bonds” such as a
hiol-Au/Ag linkage. Thus, weak amide–AgNPs in e ac ions be-
ween he PPA and he me al nanopa icle, which is ound in
o he polyme -based nanocomposi es such as poly inylpy oli-
done (PVP)-MNPs nanocomposi es we e employed. To p epa e
his poly-(R)-1-AgNPs/dodecane hiol nanocomposi es, poly-(R)-1
was complexed wi h Ag+by adding AgClO4as a sou ce o sil e
ions, and his complex was u he ans o med in o he poly-
(R)-1-AgNPs/dodecane hiol nanocomposi es using NaBH4as
educing agen and 1-dodecane hiol as cos abilizing agen . The
esul ing nanocomposi es show low-polydispe se 2.8 nm AgNPs
linea ly dis ibu ed along he PPA chain. This weak sup amolec-
ula in e ac ion be ween PPA and AgNP allows p ese ing he
dynamic beha io o poly-(R)-1wi hin he nanocomposi e, whe e
Po Mhelical senses can be effec i ely induced in he helical
Mac omol. Rapid Commun. 2022,43, 2100616 2100616 (1 o 5) © 2021 The Au ho s. Mac omolecula Rapid Communica ions published by Wiley-VCH GmbH
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polyme by ac ion o ex e nal s imuli.[40] Thus, while s ong
polyme -me al nanopa icle in e ac ions inhibi he dynamic be-
ha io o he nanocomposi e,[39] weak sup amolecula o ces p e-
se e i .[40] He ein, we will explo e he o ma ion o poly-(R)-
1-AuNPs/dodecane hiol nanocomposi es, whe e sup amolecula
amide–AuNP in e ac ions a e used o link bo h componen s o
he nanocomposi e.
2. Resul s and Discussion
In a fi s a emp , he p epa a ion o poly-(R)-1-AuNPs/
dodecane hiol nanocomposi e was ca ied ou using he
p o ocol de eloped o poly-(R)-1-AgNPs/dodecane hiol
nanocomposi e.[40] Thus, 0.5 equi o a me hanolic solu ion
o HAuCl4we e added o a chlo o o m solu ion o poly-(R)-1
(0.3 mg mL−1) o o m a poly-(R)-1/Au3+complex (Figu e 1a). A
colo change om yellow o blue is obse ed once he me al ion
is added o he polyme solu ion (Figu e 1b).
EPR s udies e ealed he p esence o a adical specie in he
polyme , which is delocalized along he polyene backbone (Fig-
u e 1d) and gene a ed by a edox p ocess a e he addi ion o he
Au3+ions. The gene a ion o adical species mus be a oided in
PPAs due o a cis o ans isome iza ion o he polyene backbone,
ha esul s in a plana iza ion o he polyme , and whe e nonheli-
cal s uc u es can be gene a ed. XPS expe imen s demons a ed
a edox p ocess when poly-(R)-1 and Au3+ions a e mixed. Thus,
Au3+is pa ially educed o Au0signals gene a ing a adical ca ion
in he PPA as in e ed p e iously by EPR s udies (Figu e 1e).
On he o he hand, ansmission elec on mic oscopy (TEM) im-
ages o he PPA/Au3+mix u e show he p esence o polydispe se
AuNPs and wi h diffe en mo phology, con o ming his edox
p ocess (Figu e 1c; Figu e S5, Suppo ing In o ma ion).
Thus, an al e na i e p o ocol mus be de eloped o p e-
pa e he poly-(R)-1-AuNPs/dodecane hiol nanocomposi e, a oid-
ing a di ec complexa ion be ween he polyme and he Au3+
ions. To su pass his p oblem, we decided o inhibi he e-
dox eac ion by deac i a ion o he Au3+ions. To do ha , a
a ia ion o he B us -Schiff in[42] p o ocol was used o p e-
pa e he poly-(R)-1-AuNPs/dodecane hiol nanocomposi e. Fi s ,
e aoc ylammonium b omide was used o ans e he Au3+
ions om an aq HAuCl4solu ion o an o ganic sol en , in his
case dichlo ome hane. Nex , poly-(R)-1and 1-dodecane hiol we e
added a a Au3+/poly-(R)-1/1-dodecane hiol a io o 1/0.4/0.8
(mol/mol/mol) o he o ganic laye and he mix u e was s i ed
o 20 min a −4°C be o e adding he educing agen .
In his solu ion mix u e, 1-dodecane hiol in e ac s wi h he
Au3+ o o m a s able complex, which a oids he PPA–Au3+in e -
ac ion and he polyme dena u aliza ion. Nex , NaBH4was added
o he dichlo ome hane solu ion and he eac ion mix u e u ned
om yellow/o ange owa ds b own/black colo , indica ing he
gene a ion o AuNPs (Figu e 2a).
The esul ing ma e ial was pu ified by p ecipi a ion wi h
oluene and cen i uga ion (see mo e de ails in he Suppo -
ing In o ma ion). Fu he pu ifica ion o he nanocomposi e
was ca ied ou by gel pe o mance ch oma og aphy (GPC),
which showed he p esence o a GPC peak ( Rpoly-(R)-1-
AuNPs/dodecane hiol =10 min, Figu e 2d) wi h sho e R han
hose ob ained o he s a ing componen s— Rpoly-(R)-1=
21 min; RAuNPs =27 min—(see ESI Figu e S13 in he Sup-
Figu e 1. a) Schema ic ep esen a ion o he o ma ion o adicals in poly-
(R)-1in p esence o HAuCl4. b) UV– is spec a o poly-(R)-1and poly-(R)-1
in p esence o HAuCl4. c) TEM images o AuNPs gene a ed by he edox
p ocess. d) EPR s udies o poly-(R)-1and poly-(R)-1in p esence o HAuCl4.
e) XPS s udies o poly-(R)-1in p esence o HAuCl4.
po ing In o ma ion). Mo eo e , addi ional GPC s udies a wo
diffe en wa eleng hs—540 (LSPR abso p ion) and 380 nm (poly-
me abso p ion)—showed he o ma ion o he nanocomposi e,
which abso bs a hose wa eleng hs, while he pa en compo-
nen s, poly-(R)-1and AuNPs abso b a 380 and 540 nm espec-
i ely (Figu e S13, Suppo ing In o ma ion).
The e o e, hese esul s indica e ha while poly-(R)-1does
no in e ac wi h Au3+/1-dodecane hiol complexes, he educ-
ion o Au3+ o Au0p omo es he in e ac ion be ween he
h ee componen s gene a ing he desi ed desi ed poly-(R)-1-
AuNPs/dodecane hiol nanocomposi e. This hyb id ma e ial ex-
hibi s excellen s abili y and can be s o ed in solid s a e unde an
a gon a mosphe e o mon hs.
Cha ac e iza ion o he poly-(R)-1-AuNPs/dodecane hiol hy-
b id ma e ial was done using diffe en echniques such as di -
e en ial scanning calo ime y (DSC), 1H-NMR, UV– is, and IR.
Mac omol. Rapid Commun. 2022,43, 2100616 2100616 (2 o 5) © 2021 The Au ho s. Mac omolecula Rapid Communica ions published by Wiley-VCH GmbH
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Figu e 2. a) Schema ic ep esen a ion o he o ma ion o poly-
(R)-1-AuNPs nanocomposi es by a a ia ion o B us -Schiff in
me hod. b) UV– is, c) FT-IR expe imen s o poly-(R)-1and poly-(R)-
1-AuNPs/dodecane hiol nanocomposi es. d) TEM images o poly-(R)-
1-AuNPs/dodecane hiol nanocomposi es (3.7 ±1.2, 93 nanopa icles).
e) Illus a ion o a poly-(R)-1-AuNPs/dodecane hiol nanocomposi es,
showing a linea and andom dis ibu ion o AuNPS along he polyme
chain.
UV– is measu emen s showed he cha ac e is ic ace o poly-
(R)-1and he p esence o an ex a UV band a 540 nm co e-
sponding o he localized su ace plasmon esonance (LSPR)
band o sphe ical AuNPs (Figu e 2b). This ac indica es he
p esence o he wo componen s in he nanocomposi e. 1H-
NMR expe imen s showed he signals co esponding o poly-
(R)-1and 1-dodecane hiol, co obo a ing he e o e he ob en-
ion o he nanocomposi e (Figu e S16, Suppo ing In o ma-
ion). In e es ingly, FT-IR s udies showed a s ong in e ac ion
be ween he anilide g oup o poly-(R)-1and he AuNPs—Δ𝜈CO
=78 cm−1;Δ𝜈NCO =16 cm−1— ac ha indica es as expec ed he
ole o he amide a poly-(R)-1in he s abiliza ion o he AuNPs
(Figu e 2c).
Once, he p esence o he nanocomposi e was demons a ed,
s uc u al s udies on he polyme we e ca ied ou o demons a e
ha i s helical s uc u e emained unal e ed du ing he o ma-
ion o he hyb id ma e ial. Thus, DSC expe imen s showed a
he mog am cha ac e is ic o a cis-cisoidal s uc u e, like he one
ob ained o he pa en PPA poly-(R)-1(Figu e S14 in he Sup-
po ing In o ma ion o de ails).
To s udy he mo phology o he agg ega e, dynamic ligh sca -
e ing (DLS) and elec on mic oscopy s udies we e ca ied ou .
DLS expe imen s indica ed he o ma ion o la ge agg ega es
compa ed o he pa en polyme —poly-(R)-1–(Figu e S12 in he
Suppo ing In o ma ion). On he o he hand, TEM s udies p o-
duced images ha showed he p esence o small, sphe ical, low-
polydispe se AuNPs (3.7 ±1.2 nm), which a e aligned along he
polyme chain and egula ly sepa a ed ≈6.1 nm ha coincide
wi h wo consecu i e helical pi ches o poly-(R)-1(Figu e 2d and
Suppo ing In o ma ion).
Nex , he dynamic beha io o he helical polyme wi hin
he nanocomposi es was analyzed by elec on ci cula dich o-
ism (ECD) and s imuli esponsi e s udies. These expe i-
men s allow de e mining how he diffe en helical enhance-
men effec s obse ed in poly-(R)-1a e affec ed once poly-(R)-1-
AuNPs/dodecane hiol is p epa ed. To do ha , ECD expe imen s
o a poly-(R)-1-AuNPs/dodecane hiol nanocomposi e dispe sion
p epa ed in chlo o o m (0.1 mg mL−1) we e ca ied ou . As ex-
pec ed, he ECD ace was null in he 300–500 nm egion, which
indica es he p esence o an axially acemic polyme wi hin he
nanocomposi e (see ESI).
The addi ion o ex e nal s imuli such as mono a-
len (Li+) o di alen (Ba2+) me al ions in a poly-(R)-1-
AuNPs/dodecane hiol/Mn+1.0/0.5 mol/mol a io induce
ei he M(CD380 <0) o P(CD380 >0) helix in he PPA simila
o hose epo ed p e iously o poly-(R)-1(Figu e 3b; Fig-
u e S19, Suppo ing In o ma ion). Compa ison o he ECD
aces ob ained o poly-(R)-1-AuNPs/dodecane hiol/Ba2+and
poly-(R)-1-AuNPs/dodecane hiol/Li+wi h hose ob ained o
poly-(R)-1/Ba2+and poly-(R)-1/Li+shows ha he helical sense
induc ion in he nanocomposi e/me al complex is smalle han
in he polyme /me al complex (Figu e 3b,c). In his case, a de-
ple ion o ca. 40% o he helix enhancemen effec o poly-(R)-1
in he nanocomposi e is obse ed, which is associa ed o a s ong
sup amolecula in e ac ion be ween he anilide g oups and he
gold nanopa icles.
Finally, he o ma ion o nanosphe es based on poly-1-
AuNPs/dodecane hiol/Mn+was explo ed using me al ions ha
ac as c osslinking agen s. Thus, dispe sions o poly-(R)-1-
AuNPs/dodecane hiol/Ba2+complexes (0.1 mg mL−1) a diffe -
en mol/mol a ios (1/0.2, 1/0.4, and 1/0.6) we e p epa ed and
s udied by DLS and su ace elec on mic oscopy (SEM). These
s udies mani es he p esence o nanosphe es, whose size and
mac oscopic chi al con en (excess o Mo Phelical sense) can
be uned by a ying he amoun o me al in he complex (Fig-
u e 3d,e; Figu e S20 o mo e de ails in he Suppo ing In o ma-
ion).
3. Conclusion
In conclusion, i was demons a ed ha i is possible o p epa e
dynamic chi al nanocomposi es based on sup amolecula in e -
ac ions be ween PPAs and gold nanopa icles—AuNP–anilide in-
e ac ions. To p epa e hese nanocomposi es, a a ia ion o he
B us –Schiff in p o ocol is necessa y o a oid he deg ada ion o
he PPA by Au3+ions. In his case, TOAB is fi s complexed o
Mac omol. Rapid Commun. 2022,43, 2100616 2100616 (3 o 5) © 2021 The Au ho s. Mac omolecula Rapid Communica ions published by Wiley-VCH GmbH
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Figu e 3. a) Schema ic ep esen a ion o helical induc ion by adding
Ba2+ o poly-(R)-1-AuNPs/dodecane hiol nanocomposi es. b) CD aces
o poly-(R)-1/Ba2+and poly-(R)-1-AuNPs/dodecane hiol/Ba2+a 0.1 mg
mL−1in CHCl3. c) Rep esen a ion o % CD in ensi y a 380 nm o
poly-(R)-1/Ba2+and poly-(R)-1-AuNPs/dodecane hiol/Ba2+.d)DLSmea-
su emen s o poly-(R)-1-AuNPs/dodecane hiol/Ba2+a 0.1 mg mL−1in
CHCl3. e) SEM images o poly-(R)-1-AuNPs/dodecane hiol/Ba2+in a
mol/mol a io (1/0.4) (Size: 200 ±24 nm, 23 pa icles).
Au3+ions, hen poly-(R)-1and he educing agen s a e added p o-
ducing he nanocomposi es which con ain small and low poly-
dispe se AuNPs (3.7 ±1.2 nm). These AuNPs line up along he
polyme chain and a e egula ly displayed a ≈6 nm, a dis ance
ha co esponds o wo consecu i e helical pi ches.
These s udies confi m ha o p epa e a dynamic helical
polyme -MNP nanocomposi e i is necessa y o conside how he
s eng h o he PPA–MNP in e ac ion affec s i s dynamic beha -
io . Thus, while s ong hiol–AuNP in e ac ions educe d ama i-
cally he dynamic beha io o he PPA, weake sup amolecula
in e ac ions main ain good s imuli esponse p ope ies in he
nanocomposi e.
These s udies a e a b eak h ough in he de elopmen o no el
hyb id ma e ials based on dynamic helical polyme s, p o iding
ules on how o a ach hese polyme s o o he ma e ials, no jus
me al nanopa icles, wi hou affec ing hei dynamic beha io . Fi-
nally, he p epa a ion o hese chi al nanocomposi es open new
possibili ies in he p epa a ion o ma e ials wi h dynamic chi al
plasmon esponse, whe e he dynamic cha ac e o he PPA could
be ans e ed o he me al nanopa icles.
Suppo ing In o ma ion
Suppo ing In o ma ion is a ailable om he Wiley Online Lib a y o om
he au ho .
Acknowledgemen s
The au ho s hank Se icio de Mic oscopía Elec ónica (RIAIDT, USC) and
Se icio de Nano ecnología y Análisis de Supe ficies (CACTI, UVIGO).
Financial suppo om AEI (PID2019-109733GB-I00), Xun a de Galicia
(ED431C 2018/30, Cen o Singula de In es igación de Galicia ac ed-
i ación 2019–2022, ED431G 2019/03, Beca Leona do a In es igado es y
C eado es Cul u ales 2020 de la Fundación BBVA and he Eu opean Re-
gional De elopmen Fund (ERDF) and is g a e ully acknowledged. N.-M.
hanks MICINN o a FPI con ac (BES-2016-078107).
Conflic o In e es
The au ho s decla e no conflic o in e es .
Da a A ailabili y S a emen
Da a a ailable in a icle supplemen a y ma e ial
Keywo ds
chi ali y, gold nanopa icles, helical polyme s, nanocomposi es
Recei ed: Sep embe 22, 2021
Re ised: Oc obe 26, 2021
Published online: No embe 17, 2021
[1] S. Zhang, R. Ge yak, J. Geldmeie , S. Kim, V. Tsuk uk, Chem. Re . 2017,
117, 12942.
[2] M. Molina, M. Asadian-Bi jand, J. Balach, J. Be guei o, E. Miceli, M.
Calde on, Chem.Soc.Re .2015,17, 6161.
[3] M. Ca il, D. Pad o, P. del Pino, C. Ca illo-Ca ion, M. Gallego, J. W.
Pa ak, Na . Commun. 2017,8, 1542.
[4] Y. Zhou, H. Sun, S. Ma ysiak, J. Ren, X. Qu, Angew. Chem., In . Ed.
2018,57, 16791.
[5] G. Zheng, Z. Bao, J. Pé ez-Jus e, D. Ruolan, W. Liu, J. Dai, W. Zhang,
L. Lee, K. Y. Wong, Angew. Chem., In . Ed. 2018,57, 16452.
[6] A. Sánchez-Iglesias, X. Zhuo, W. Alb ech , S. Bals, L. Liz-Ma zán, ACS
Ma e . Le . 2020,2, 1246.
Mac omol. Rapid Commun. 2022,43, 2100616 2100616 (4 o 5) © 2021 The Au ho s. Mac omolecula Rapid Communica ions published by Wiley-VCH GmbH
www.ad ancedsciencenews.com www.m c-jou nal.de
[7] J. Mosque a, Y. Zhao, H. J. Jang, N. Xie, C. Xu, N. Ko o , L. M. Liz-
Ma zán, Ad . Func . Ma e . 2020,30, 1902082.
[8] C. Pigliacelli, R. Sánchez-Fe nández, M. D. Ga cía, C. Peinado , E.
Pazos, Chem. Commun. 2020,56, 8000.
[9] J. Lu, Y. Xue, K. Be na dino, N. N. Zhang, W. R. Gomes, N. S. Ramesa ,
S.Liu,Z.Hu,T.Sun,A.Fa iasdeMou a,N.A.Ko o ,K.Liu,Science
2021,371, 1368.
[10] E. Yashima, K. Maeda, H. Lida, Y. Fu usho, K. Nagai, Chem. Re . 2009,
109, 6102.
[11] E. Yashima, K. Maeda, Mac omolecules 2008,41,3.
[12] B. M. Rosen, C. J. Wilson, D. A. Wilson, M. Pe e ca, M. R. Imam, V.
Pe cec, Chem. Re . 2009,109, 6275.
[13] F. F ei e, E. Quiñoá, R. Rigue a, Chem. Re . 2016,116, 1242.
[14] F. F ei e, J. M. Seco, E. Quiñoá, R. Rigue a, J. Am. Chem. Soc. 2012,
134, 19374.
[15] X. Guan, S. Wang, G. Shi, J. Zhang, X. Wan, Mac omolecules 2021,54,
4592.
[16] H. Huang, H. Duan, L. Yin, D. Qi, J. Xue, Y. Zhang, J. Deng, Mac o-
molecules 2020,53, 6002.
[17] E. Suá ez-Picado, E. Quiñoá, R. Rigue a, F. F ei e, Chem. Ma e . 2018,
30, 6908.
[18] S. A ias, M. Núñez-Ma inez, E. Quiñoá, R. Rigue a, F. F ei e, Polym.
Chem. 2017,8, 3740.
[19] K. Echizen, T. Taniguchi, T. Ta suya Nishimu a, K. Maeda, J. Am.
Chem. Soc. 2021,143, 3604.
[20] M. Alzubi, S. A ias, I. louzao, E. Quiñoá, R. Rigue a, F. F ei e, Chem.
Commun. 2017,53, 8573.
[21] F. Rey-Ta ío, R. Rod íguez, E. Quiñoá, R. Rigue a, F. F ei e, Angew.
Chem., In . Ed. 2021,60, 8095.
[22] Z. Fe nández, B. Fe nández, E. Quiñoá, R. Rigue a, F. F ei e, Chem.
Sci. 2020,11, 7182.
[23] S. A ias, M. Nuñez-Ma ínez, E. Quiñoá, R. Rigue a, F. F ei e, Small
2017,13, 1602398
[24] T. Ikai, T. Ku ake, S. Okuda, K. Maeda, E. Yashima, Angew. Chem., In .
Ed. 2021,60, 4625.
[25] L. Zhou, L. Chong-Long, G. Run-Tan, K. Shu-Ming, X. Lei, X. Xun-Hui,
L. Na, W. Zong-Quan, Mac omolecules 2021,54, 679.
[26] R. Rod íguez, E. Suá ez-Picado, E. Quiñoá, R. Rigue a, F. F ei e,
Angew. Chem., In . Ed. 2020,59, 8616.
[27] E. Yashima, N. Ousaka, D. Tau a, K. Shimomu a, T. Ikai, K. Maeda,
Chem. Re . 2016,116, 13752.
[28] T. Nakano, Y. Okamo o, Chem. Re . 2001,101, 4013.
[29] E.Schwa z,M.Koep ,H.J.Ki o,R.J.M.Nol e,A.E.Rowan,Polym.
Chem. 2011,2, 33.
[30] K. Maeda, M. Nozaki, K. Hashimo o, K. Shimomu a, D. Hi ose, T.
Nishimu a, G. Wa anabe, E. Yashima, J. Am. Chem. Soc. 2020,142,
7668.
[31] E. Yashima, K. Maeda, Y. Fu usho, Acc. Chem. Res. 2008,41, 1166.
[32] R. Ishida e, A. J. Ma k oo , K. Maeda, E. Yashima, J. Am. Chem. Soc.
2019,141, 7605.
[33] R. Rod íguez, S. A ias, E. Quiñoá, R. Rigue a, F. F ei e, Nanoscale
2017,9, 17752.
[34] M. Alzubi, S. A ias, I. Louzao, E. Quiñoá, R. Rigue a, F. F ei e, Chem.
Commun. 2017,53, 8573.
[35] S. A ias, J. Be guei o, F. F ei e, E. Quiñoá, R. Rigue a, Small 2016,12,
238.
[36] L. Palomo, R. Rod íguez, S. Medina, E. Quiñoá, J. Casado, F. F ei e,
F. J. Ramí ez, Angew. Chem., In . Ed. 2020,59, 9080.
[37] E. Suá ez-Picado, E. Quiñoá, R. Rigue a, F. F ei e, Angew. Chem., In .
Ed. 2020,59, 4537.
[38] Y. Li, L. Xu, S. Kang, L. Zhou, N. Liu, Z.- Q. Wu, Angew. Chem., In .
Ed. 2021,60, 7174.
[39] J. Be guei o, M. Nuñez-Ma ínez, S. A ias, E. Quiñoá, R. Rigue a, F.
F ei e, Nanoscale Ho iz. 2020,5, 495.
[40] M. Nuñez-Ma ínez, S. A ias, E. Quiñoá, R. Rigue a, F. F ei e, Chem.
Ma e . 2021,33, 4805.
[41] C. Zhang, C. Song, W. Yang, J. Deng, Mac omol. Rapid Commun. 2013,
34, 1319.
[42] M. B us , M. Walke , D. Be hell, D. J. Schiff in, R. J. Whyman, Chem.
Commun. 1994, 801.
Mac omol. Rapid Commun. 2022,43, 2100616 2100616 (5 o 5) © 2021 The Au ho s. Mac omolecula Rapid Communica ions published by Wiley-VCH GmbH
