For simplicity's sake, I would probably do a hash of arrays if I was going to store them all beforehand, but why not just process line by line... for example...

open(LIST, "list.txt") or die $!;
my @files;
while(<LIST>) {
  s/^'//;
  s/'\n?$//;
  @files = split /','/, $_;
  my $email = shift @files;
  ### $email holds email, @files holds files, so put
  ### code here to send email accordingly 
}
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